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3-Azido-3-deoxy-5-O-triphenylmethylthymidine is a chemical compound derived from thymidine, featuring a triphenylmethyl group at the 5-O position and an azido group at the 3 position on the deoxyribose ring. This modification endows the compound with unique antiviral and antitumor properties, making it a valuable subject in nucleotide analogs research.

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  • 29706-84-1 Structure
  • Basic information

    1. Product Name: 3-Azido-3-deoxy-5-O-triphenylmethylthymidine
    2. Synonyms: 3-Azido-3-deoxy-5-O-triphenylmethylthymidine;3''-AZIDO-3''-DEOXY-5''-O-TRITYLTHYMIDINE;1-((2R,4S,5S)-4-azido-5-((trityloxy)Methyl)tetrahydrofuran-2-yl)-5-MethylpyriMidine-2,4(1H,3H)-dione;1-(4-azido-5-trityloxymethyl-tetrahdyro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione;3'-Azido-5'-O-trityl-2',3'-dideoxy-5-methyluridine;1-(4-azido-5-((trityloxy)methyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione;Zidovudine impurity Q
    3. CAS NO:29706-84-1
    4. Molecular Formula: C29H27N5O4
    5. Molecular Weight: 509.563
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 29706-84-1.mol
    9. Article Data: 12
  • Chemical Properties

    1. Melting Point: 103-104 °C(Solv: toluene (108-88-3))
    2. Boiling Point: N/A
    3. Flash Point: N/A
    4. Appearance: /
    5. Density: N/A
    6. Refractive Index: N/A
    7. Storage Temp.: N/A
    8. Solubility: N/A
    9. CAS DataBase Reference: 3-Azido-3-deoxy-5-O-triphenylmethylthymidine(CAS DataBase Reference)
    10. NIST Chemistry Reference: 3-Azido-3-deoxy-5-O-triphenylmethylthymidine(29706-84-1)
    11. EPA Substance Registry System: 3-Azido-3-deoxy-5-O-triphenylmethylthymidine(29706-84-1)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 29706-84-1(Hazardous Substances Data)

29706-84-1 Usage

Uses

Used in Pharmaceutical Research:
3-Azido-3-deoxy-5-O-triphenylmethylthymidine is used as a nucleotide analog for its antiviral and antitumor properties due to its ability to inhibit DNA and RNA synthesis. This leads to the disruption of viral replication and the proliferation of cancer cells, offering potential therapeutic benefits in treating viral infections and various types of cancer.
Used in Drug Development:
3-Azido-3-deoxy-5-O-triphenylmethylthymidine's triphenylmethyl group enhances its stability and bioavailability, making 3-Azido-3-deoxy-5-O-triphenylmethylthymidine a promising candidate for further pharmaceutical development. Its potential applications include the creation of new antiviral and antitumor drugs, as well as the improvement of existing treatments through enhanced efficacy and reduced side effects.
Used in Antiviral Applications:
3-Azido-3-deoxy-5-O-triphenylmethylthymidine is used as an antiviral agent for its ability to inhibit viral replication by disrupting DNA and RNA synthesis. This makes it a valuable tool in the development of treatments for a wide range of viral infections, including those caused by RNA and DNA viruses.
Used in Antitumor Applications:
In the field of oncology, 3-Azido-3-deoxy-5-O-triphenylmethylthymidine is used as an antitumor agent, targeting the inhibition of cancer cell proliferation by interfering with DNA synthesis. Its potential to disrupt the growth and spread of cancer cells positions it as a candidate for the development of novel cancer therapies.
Used in Biochemistry and Molecular Biology Research:
3-Azido-3-deoxy-5-O-triphenylmethylthymidine's unique structure and properties also make it a valuable tool in biochemical and molecular biology research. It can be used to study the mechanisms of DNA and RNA synthesis, as well as the effects of nucleotide analogs on various biological processes. This research can contribute to a deeper understanding of the molecular basis of viral infections and cancer, and may lead to the discovery of new therapeutic targets and strategies.

Check Digit Verification of cas no

The CAS Registry Mumber 29706-84-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,9,7,0 and 6 respectively; the second part has 2 digits, 8 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 29706-84:
(7*2)+(6*9)+(5*7)+(4*0)+(3*6)+(2*8)+(1*4)=141
141 % 10 = 1
So 29706-84-1 is a valid CAS Registry Number.

29706-84-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name 1-[(2R,4S,5S)-4-azido-5-(trityloxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione

1.2 Other means of identification

Product number -
Other names 3-Azido-3-deoxy-5-O-triphenylmethylthymidine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:29706-84-1 SDS

29706-84-1Synthetic route

5'-O-trityl-2,3'-anhydrothymidine
25442-42-6

5'-O-trityl-2,3'-anhydrothymidine

1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine
29706-84-1

1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine

Conditions
ConditionsYield
With lithium azide In N,N-dimethyl-formamide at 100℃;96%
With sodium azide In water; N,N-dimethyl-formamide for 15h; Heating;80%
With sodium azide In dimethyl sulfoxide at 110℃; for 24h; Large scale reaction;
Multi-step reaction with 2 steps
1.1: sodium azide / dimethyl sulfoxide / 24 h / 110 °C / Large scale reaction
1.2: 2.5 h / 77 °C / Large scale reaction
2.1: pyridine / 1 h / 70 - 75 °C
View Scheme
3'-azido-2',3'-deoxythymidine
30516-87-1

3'-azido-2',3'-deoxythymidine

trityl chloride
76-83-5

trityl chloride

1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine
29706-84-1

1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine

Conditions
ConditionsYield
With pyridine at 45℃;95%
With pyridine at 70 - 75℃; for 1h;41.18 g
C35H31N3O9S

C35H31N3O9S

1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine
29706-84-1

1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine

Conditions
ConditionsYield
With sodium azide In N,N-dimethyl-formamide at 20℃; for 24h;94%
1-(2-deoxy-3-O-methanesulfonyl-5-O-trityl-β-D-threo-pentofuranosyl)thymine
104218-44-2

1-(2-deoxy-3-O-methanesulfonyl-5-O-trityl-β-D-threo-pentofuranosyl)thymine

1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine
29706-84-1

1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine

Conditions
ConditionsYield
With sodium azide In ethylene glycol at 120℃; for 0.75h;87%
With lithium azide In N,N-dimethyl-formamide at 80℃; for 4h;
5'-O-trityldeoxyxylothymidine
55612-11-8

5'-O-trityldeoxyxylothymidine

A

1-(3-Azido-2,3-dideoxy-5-O-trityl-β-D-threo-pentofuranosyl)thymine
66503-47-7

1-(3-Azido-2,3-dideoxy-5-O-trityl-β-D-threo-pentofuranosyl)thymine

B

1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine
29706-84-1

1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine

Conditions
ConditionsYield
With lithium azide; carbon tetrabromide; triphenylphosphine In N,N-dimethyl-formamide for 43h; Ambient temperature;A n/a
B 67%
1-(2-deoxy-3-O-methanesulfonyl-5-O-trityl-β-D-ribopentofuranosyl)thymine
42214-24-4

1-(2-deoxy-3-O-methanesulfonyl-5-O-trityl-β-D-ribopentofuranosyl)thymine

A

5'-O-trityl-2,3'-anhydrothymidine
25442-42-6

5'-O-trityl-2,3'-anhydrothymidine

B

1-(3-Azido-2,3-dideoxy-5-O-trityl-β-D-threo-pentofuranosyl)thymine
66503-47-7

1-(3-Azido-2,3-dideoxy-5-O-trityl-β-D-threo-pentofuranosyl)thymine

C

1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine
29706-84-1

1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine

Conditions
ConditionsYield
With lithium azide In N,N-dimethyl-formamide at 100℃; for 5h;A 15%
B 48%
C 5%
With lithium azide In N,N-dimethyl-formamide at 150℃; for 0.5h;A 25%
B 25%
C 32%
5'-O-tritylthymidine
7791-71-1

5'-O-tritylthymidine

1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine
29706-84-1

1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine

Conditions
ConditionsYield
With sodium azide; triethylamine; tetra-(n-butyl)ammonium iodide In N,N-dimethyl-formamide for 12h; Heating;47%
Multi-step reaction with 3 steps
1: 95 percent / pyridine / 15 h / 0 °C
2: 85 percent / potassium phthalimide / dimethylformamide; H2O / 3 h / 90 °C
3: 80 percent / NaN3 / dimethylformamide; H2O / 15 h / Heating
View Scheme
1-(2-deoxy-3-O-methanesulfonyl-5-O-trityl-β-D-ribopentofuranosyl)thymine
42214-24-4

1-(2-deoxy-3-O-methanesulfonyl-5-O-trityl-β-D-ribopentofuranosyl)thymine

A

6,3'-Imino-1-(2,3-dideoxy-5-O-trityl-β-D-threo-pentofuranosyl)thymine
73971-78-5

6,3'-Imino-1-(2,3-dideoxy-5-O-trityl-β-D-threo-pentofuranosyl)thymine

B

1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine
29706-84-1

1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine

Conditions
ConditionsYield
With sodium azide In N,N-dimethyl-formamide for 24h; Heating;A 43%
B 41%
1-(2-deoxy-3-O-methanesulfonyl-5-O-trityl-β-D-ribopentofuranosyl)thymine
42214-24-4

1-(2-deoxy-3-O-methanesulfonyl-5-O-trityl-β-D-ribopentofuranosyl)thymine

NaN3

NaN3

1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine
29706-84-1

1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine

Conditions
ConditionsYield
In N,N-dimethyl-formamide for 24h; Heating;43%
1-(3'-iodo-2',3'-dideoxy-5'-O-trityl-β-D-erythro-pentofuranosyl)thymine
25442-44-8

1-(3'-iodo-2',3'-dideoxy-5'-O-trityl-β-D-erythro-pentofuranosyl)thymine

A

1-(3-Azido-2,3-dideoxy-5-O-trityl-β-D-threo-pentofuranosyl)thymine
66503-47-7

1-(3-Azido-2,3-dideoxy-5-O-trityl-β-D-threo-pentofuranosyl)thymine

B

1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine
29706-84-1

1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine

Conditions
ConditionsYield
With sodium azide In N,N-dimethyl-formamide at 100℃; for 0.5h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
5'-O-trityldeoxyxylothymidine
55612-11-8

5'-O-trityldeoxyxylothymidine

1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine
29706-84-1

1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: pyridine / 9 h / 0 - 20 °C
2: LiN3 / dimethylformamide / 4 h / 80 °C
View Scheme
1-(2-deoxy-3-O-methanesulfonyl-5-O-trityl-β-D-ribopentofuranosyl)thymine
42214-24-4

1-(2-deoxy-3-O-methanesulfonyl-5-O-trityl-β-D-ribopentofuranosyl)thymine

1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine
29706-84-1

1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 85 percent / potassium phthalimide / dimethylformamide; H2O / 3 h / 90 °C
2: 80 percent / NaN3 / dimethylformamide; H2O / 15 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: sodium carbonate / methanol; water / Reflux
2: lithium azide / N,N-dimethyl-formamide / 100 °C
View Scheme
AZT-sodium

AZT-sodium

1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine
29706-84-1

1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: water / 70 - 97 °C
2: hydrogenchloride / water / 75 °C / Large scale reaction
3: pyridine / 1 h / 70 - 75 °C
View Scheme
AZT guanidine salt
162404-30-0

AZT guanidine salt

1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine
29706-84-1

1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogenchloride / water / 75 °C / Large scale reaction
2: pyridine / 1 h / 70 - 75 °C
View Scheme
2'-bromothymidine
95585-76-5

2'-bromothymidine

1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine
29706-84-1

1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: pyridine / 60 °C
2: pyridine / dichloromethane / 0 - 5 °C
3: hydrogen; triethylamine / methanol / 20 - 40 °C
4: sodium carbonate / methanol; water / Reflux
5: lithium azide / N,N-dimethyl-formamide / 100 °C
View Scheme
trityl chloride
76-83-5

trityl chloride

1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine
29706-84-1

1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: pyridine / 60 °C
2: pyridine / dichloromethane / 0 - 5 °C
3: hydrogen; triethylamine / methanol / 20 - 40 °C
4: sodium carbonate / methanol; water / Reflux
5: lithium azide / N,N-dimethyl-formamide / 100 °C
View Scheme
5'-trityl-2'-bromothymidine

5'-trityl-2'-bromothymidine

1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine
29706-84-1

1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: pyridine / dichloromethane / 0 - 5 °C
2: hydrogen; triethylamine / methanol / 20 - 40 °C
3: sodium carbonate / methanol; water / Reflux
4: lithium azide / N,N-dimethyl-formamide / 100 °C
View Scheme
5'-trityl-3'-methylsulfonyl-2'-bromothymidine

5'-trityl-3'-methylsulfonyl-2'-bromothymidine

1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine
29706-84-1

1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: hydrogen; triethylamine / methanol / 20 - 40 °C
2: sodium carbonate / methanol; water / Reflux
3: lithium azide / N,N-dimethyl-formamide / 100 °C
View Scheme
1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine
29706-84-1

1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine

3'-azido-2',3'-deoxythymidine
30516-87-1

3'-azido-2',3'-deoxythymidine

Conditions
ConditionsYield
With silica gel; trifluoroacetic acid In methanol; chloroform95%
With hydrogenchloride In methanol; water at 20℃; for 3h;95%
With hydrogenchloride In acetic acid at 20℃; for 2h;49%
With sodium periodate In acetone at 50℃; for 20h;
1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine
29706-84-1

1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine

3'-amino-3'-deoxy-5'-O-triphenylmethyl-β-D-thymidine
124355-25-5

3'-amino-3'-deoxy-5'-O-triphenylmethyl-β-D-thymidine

Conditions
ConditionsYield
With sodium tetrahydroborate In isopropyl alcohol at 82℃; for 14h;93%
With thiophenol; triethylamine; tin(ll) chloride In acetonitrile for 0.5h; Ambient temperature;85%
With ammonium formate; palladium on activated charcoal In methanol for 2.5h; Heating;76%
N-methoxy-N-methyl-2-propynamide
130250-60-1

N-methoxy-N-methyl-2-propynamide

1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine
29706-84-1

1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine

C34H34N6O6

C34H34N6O6

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In acetonitrile for 3h; Inert atmosphere; Reflux; stereoselective reaction;91%
N,N-dimethylformamide diethyl diacetal
1188-33-6

N,N-dimethylformamide diethyl diacetal

1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine
29706-84-1

1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine

3'-azido-3'-deoxy-3-ethyl-5'-O-tritylthymidine

3'-azido-3'-deoxy-3-ethyl-5'-O-tritylthymidine

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 100℃; for 24h;82%
allyl bromide
106-95-6

allyl bromide

1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine
29706-84-1

1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine

3-allyl-3'-azido-3'-deoxy-5'-O-tritylthymidine

3-allyl-3'-azido-3'-deoxy-5'-O-tritylthymidine

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 4h;78%
2-(2-(prop-2-yn-1-yloxy)ethoxy)ethyl methanesulfonate
943726-01-0

2-(2-(prop-2-yn-1-yloxy)ethoxy)ethyl methanesulfonate

1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine
29706-84-1

1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine

4-[2-(2-fluoroethoxy)ethoxymethyl]-1-(5-O-trityl-2-deoxythymidin-3-yl)-1H-[1,2,3]triazole

4-[2-(2-fluoroethoxy)ethoxymethyl]-1-(5-O-trityl-2-deoxythymidin-3-yl)-1H-[1,2,3]triazole

Conditions
ConditionsYield
Stage #1: 2-(2-(prop-2-yn-1-yloxy)ethoxy)ethyl methanesulfonate With tetrabutyl ammonium fluoride In tert-butyl alcohol at 100℃; for 0.333333h;
Stage #2: 1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine With copper(II) sulfate; sodium L-ascorbate In water; tert-butyl alcohol at 20℃; for 0.5h; Huisgen 1,3-dipolar cycloaddition; Further stages.;
73%
prenyl bromide
870-63-3

prenyl bromide

1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine
29706-84-1

1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine

3'-azido-3'-deoxy-3-(2-methyl-2-butenyl)-5'-O-tritylthymidine

3'-azido-3'-deoxy-3-(2-methyl-2-butenyl)-5'-O-tritylthymidine

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 60℃; for 4h;64%
5'-O-trityl-2,3'-anhydrothymidine
25442-42-6

5'-O-trityl-2,3'-anhydrothymidine

1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine
29706-84-1

1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine

A

3'-azido-2',3'-deoxythymidine
30516-87-1

3'-azido-2',3'-deoxythymidine

B

thymin
65-71-4

thymin

C

3'-N''-(3'''-azido-3'''-deoxythymid-3''-yl)-3'-deoxythymidine

3'-N''-(3'''-azido-3'''-deoxythymid-3''-yl)-3'-deoxythymidine

Conditions
ConditionsYield
With potassium carbonate In dimethyl sulfoxide at 108℃; for 24h;A 31 %Chromat.
B 16 %Chromat.
C 8.6%
1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine
29706-84-1

1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine

3'-amino-3'-deoxythymidine
52450-18-7

3'-amino-3'-deoxythymidine

Conditions
ConditionsYield
With hydrogen; acetic acid; palladium on activated charcoal Yield given. Multistep reaction;
Multi-step reaction with 2 steps
1: 93 percent / sodium borohydride / propan-2-ol / 14 h / 82 °C
2: Dowex 50Wx2 (H+) / methanol; H2O
View Scheme
Multi-step reaction with 2 steps
1: H2 / 10percent Pd-C / ethanol / 24 h / 825.07 Torr
2: 98percent HCO2H / 0.08 h / 70 °C
View Scheme
1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine
29706-84-1

1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine

1-((2R,4S,5S)-4-Azido-5-trityloxymethyl-tetrahydro-furan-2-yl)-4-chloro-5-methyl-1H-pyrimidin-2-one

1-((2R,4S,5S)-4-Azido-5-trityloxymethyl-tetrahydro-furan-2-yl)-4-chloro-5-methyl-1H-pyrimidin-2-one

Conditions
ConditionsYield
With 1-methyl-1H-imidazole; trichlorophosphate In pyridine; acetonitrile for 2h; Ambient temperature;
1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine
29706-84-1

1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine

1-((2R,4S,5S)-4-Azido-5-trityloxymethyl-tetrahydro-furan-2-yl)-4-hydroxyamino-5-methyl-1H-pyrimidin-2-one

1-((2R,4S,5S)-4-Azido-5-trityloxymethyl-tetrahydro-furan-2-yl)-4-hydroxyamino-5-methyl-1H-pyrimidin-2-one

Conditions
ConditionsYield
With 1-methyl-1H-imidazole; hydroxylamine hydrochloride; triethylamine; trichlorophosphate 1.) pyridine, RT, 30 min, 2.) pyridine, H2O, RT, 7 h; Multistep reaction;
1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine
29706-84-1

1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine

trimethylphosphane
594-09-2

trimethylphosphane

C32H36N3O4P

C32H36N3O4P

Conditions
ConditionsYield
In toluene for 1h; Ambient temperature;
2-(2-(prop-2-yn-1-yloxy)ethoxy)ethyl methanesulfonate
943726-01-0

2-(2-(prop-2-yn-1-yloxy)ethoxy)ethyl methanesulfonate

1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine
29706-84-1

1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine

C36H38(18)FN5O6

C36H38(18)FN5O6

Conditions
ConditionsYield
Stage #1: 2-(2-(prop-2-yn-1-yloxy)ethoxy)ethyl methanesulfonate With tetrabutylammonium bicarbonate In acetonitrile; tert-butyl alcohol at 100℃; for 0.333333h;
Stage #2: 1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine With copper(II) sulfate; sodium L-ascorbate In water; acetonitrile; tert-butyl alcohol at 20℃; for 0.166667h; Huisgen 1,3-dipolar cycloaddition; Further stages.;
1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine
29706-84-1

1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine

4-[2-(2-fluoroethoxy)ethoxymethyl]-1-(2-deoxythymidin-3-yl)-1H-[1,2,3]triazole

4-[2-(2-fluoroethoxy)ethoxymethyl]-1-(2-deoxythymidin-3-yl)-1H-[1,2,3]triazole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: 49 percent / HCl / acetic acid / 2 h / 20 °C
2.1: TBAF / 2-methyl-propan-2-ol / 0.33 h / 100 °C
2.2: 74 percent / CuSO4*5H2O; sodium ascorbate / H2O; 2-methyl-propan-2-ol / 0.5 h / 20 °C
View Scheme
1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine
29706-84-1

1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine

C45H40N4O6S

C45H40N4O6S

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: H2 / 10 percent Pd/C / ethanol / 4 h
2: CH2Cl2 / 2 h / 20 °C
View Scheme
1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine
29706-84-1

1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine

[(2S,3S,5R)-5-(5-Methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-trityloxymethyl-tetrahydro-furan-3-yl]-carbamic acid tert-butyl ester

[(2S,3S,5R)-5-(5-Methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-trityloxymethyl-tetrahydro-furan-3-yl]-carbamic acid tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: toluene / 1 h / Ambient temperature
2: toluene / 5 h / -20 - 20 °C
View Scheme
1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine
29706-84-1

1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine

1-((E)-3-Ethoxy-acryloyl)-3-[(2S,3S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-trityloxymethyl-tetrahydro-furan-3-yl]-urea
227084-00-6

1-((E)-3-Ethoxy-acryloyl)-3-[(2S,3S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-trityloxymethyl-tetrahydro-furan-3-yl]-urea

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 85 percent / SnCl2, PhSH, Et3N / acetonitrile / 0.5 h / Ambient temperature
2: 90 percent / benzene; dimethylformamide / 2 h / Ambient temperature
View Scheme

29706-84-1Relevant articles and documents

Method for synthesizing zidovudine azide intermediate based on continuous flow micro-reaction technology

-

Paragraph 0057-0086, (2021/10/05)

The method comprises the following steps: (1) mixing a zidovudine oxygen bridge, a nitriding reagent and a solvent, dissolving a zidovudine oxygen bridge and a azide reagent in the solvent to prepare a reaction raw material solution. (2) The reaction raw material solution is fed into a microchannel reactor for reaction to obtain a product solution containing a zidovudine azide intermediate. By adopting the micro-channel reactor as the core reaction equipment, continuous nitriding reaction can be carried out, the dosage of the nitriding reagent is reduced, the reaction rate is accelerated, and the reaction risk is reduced.

Intermediate preparation zidovudines and method

-

Paragraph 0057; 0066; 0067, (2017/02/09)

Disclosed is a method for preparing zidovudine (B). The method comprises the following steps: 1) 2'-halothymidine (A) is used as the raw material to obtain a compound of formula (I) by protecting the hydroxyl group thereof in the 5'-position; 2) the compound of formula (I) is subjected to the acylation of the hydroxyl group in the 3'-position to obtain a compound of formula (VI); 3) the compound of formula (VI) is dehalogenated to obtain a compound of formula (111); 4) the compound of formula (III) is subjected to an elimination reaction to obtain a compound of formula (IV); 5) the compound of formula (IV) is subjected to an azidation reaction to obtain a compound of formula (V); and 6) the compound of formula (V) is deprotected to obtain zidovudine (B); the specific reaction formula being shown in (C)below. In the formulae: X is a halogen, P1 is a protecting group for hydroxyl; and P2 is C1-C4 alkylsulfonyl, fluoro-C1-C4 alkylsulfonyl, arylsulfonyl or -CS-R, wherein R is C1-C4 alkyl.

Serendipitous discovery of a zidovudine guanidine complex: A superior process for the production of zidovudine

Radatus, Bruno K.

experimental part, p. 1281 - 1286 (2012/01/13)

A superior process for the commercial production of zidovudine (AZT) has been developed. It was discovered that an AZT-guanidine complex formed when a crude zidovudine solution was treated with guanidine. This readily precipitated from protic solvents resulting in the exclusion of impurities and permitted the development of a superior isolation and purification of AZT.

A simple one-pot procedure for the direct conversion of alcohols into azides using TsIm

Soltani Rad, Mohammad Navid,Behrouz, Somayeh,Khalafi-Nezhad, Ali

, p. 3445 - 3449 (2008/02/10)

A facile and efficient method for one-pot conversion of alcohols into azides using N-(p-toluenesulfonyl)imidazole (TsIm) is described. In this method, alcohols are refluxed with a mixture of NaN3, TsIm and triethylamine in the presence of catalytic amounts of tetra-n-butylammonium iodide (TBAI) in DMF affording the corresponding alkyl azides in good yields. This methodology is highly efficient for various structurally diverse alcohols with selectivity for ROH: 1° > 2° > 3°.

An efficient F-18 labeling method for PET study: Huisgen 1,3-dipolar cycloaddition of bioactive substances and F-18-labeled compounds

Sirion, Uthaiwan,Kim, Hee Jun,Lee, Jae Hak,Seo, Jai Woong,Lee, Byoung Se,Lee, Sang Ju,Oh, Seung Jun,Chi, Dae Yoon

, p. 3953 - 3957 (2008/02/04)

The Cu(I)-catalyzed, 1,3-dipolar cycloaddition reaction was applied successfully to the synthesis of small, F-18-labeled biomolecules, and an optimal condition was developed for one-pot, two-step reaction without any interim purifications. This technique was employed in various F-18-labeled, 1,2,3-triazole syntheses with high radiochemical yield.

An efficient synthesis of 3′-amino-3′-deoxythymidine derivatives

Seregin,Chudinov,Yurkevich,Shvets

, p. 135 - 138 (2007/10/03)

An efficient method of reduction of 3′-azido-3′-deoxythymidine and its 5′-protected derivatives to 3′-aminothymidine derivatives on a palladium catalyst using ammonium formate as a source of hydrogen was suggested.

Solid-phase synthesis of positively charged deoxynucleic guanidine (DNG) oligonucleotide mixed sequences

Reddy, Putta Mallikarjuna,Bruice, Thomas C.

, p. 1281 - 1285 (2007/10/03)

Positively charged DNG oligonucleotide mixed sequences containing A/T bases were prepared by solid-phase synthesis. Synthesis proceeds in 3′→5′ direction and involves coupling of 3′-Fmoc protected thiourea in the presence of HgCl2/TEA with the corresponding 5′-amine of the growing oligo chain. DNG binding characteristics with complementary DNA and with itself have been evaluated.

Uracil- and thymine-substituted thymidine and uridine derivatives

Costa, Anna M.,Faja, Montserrat,Farras, Jaume,Vilarrasa, Jaume

, p. 1835 - 1838 (2007/10/03)

The four possible 3'-uracil-1-yl and 3'-thymin-1-yl derivatives of 3'- deoxythymidine and the four analogous derivatives of 2'-deoxyuridine have been synthesised from thymidine and uridine, respectively. Advantages of the 2-(methoxycarbonyl)vinyl group to prevent the formation of anhydronucleosides and SnCl2/PhSH/Et3N in relation to H2/Pd for the reduction of most azido groups are disclosed.

Synthesis and biological activity of 3'-azido- and 3'-amino substituted nucleoside analogs

Colla,Herdewijn,De Clercq,et al.

, p. 295 - 301 (2007/10/02)

The product distribution obtained in the reaction of 1-(5-0-trityl-0-mesyl-2-deoxy-β-D-erythro-pentofuranosyl)-2,4-(1H, 3H)-pyrimidinedione with lithium azide in N, N'-dimethylformamide at 100°C depends on the nature of the substituent in 5. The results may be explained by a difference in the acidity of the pyrimidinedione. The reaction of the more acidic nucleosides (X = I, F) appears to proceed preferentially through the 2,3'-anhydro intermediate, whereas for the less acidic products (X = H, CH3) direct nucleophilic displacement by the azide ion predominates. The different 3'-azidfo derivatives were reduced to 3'-amino compounds. All 3'-azido- and 3'-aminopyrimidine nucleosides were tested against herpes simplex virus, vaccinia and vesicular stomatitis virus and on murine L1210 cell growth. None of the substances exhibited significant activity.

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