29706-84-1

Basic information

• Product Name: 3-Azido-3-deoxy-5-O-triphenylmethylthymidine
• 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
• CAS NO: 29706-84-1
• Molecular Formula: C₂₉H₂₇N₅O₄
• Molecular Weight: 509.563
• Mol File: 29706-84-1.mol
• Article Data: 12

Chemical Properties

• Melting Point: 103-104 °C(Solv: toluene (108-88-3))
• Appearance: /
• CAS DataBase Reference: 3-Azido-3-deoxy-5-O-triphenylmethylthymidine(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Azido-3-deoxy-5-O-triphenylmethylthymidine(29706-84-1)
• EPA Substance Registry System: 3-Azido-3-deoxy-5-O-triphenylmethylthymidine(29706-84-1)

Safety Data

• Hazardous Substances Data: 29706-84-1(Hazardous Substances Data)

Usage

Description

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.

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.

Synthetic route

5'-O-trityl-2,3'-anhydrothymidine (25442-42-6) → 1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine (29706-84-1)

Conditions	Yield
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) + trityl chloride (76-83-5) → 1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine (29706-84-1)

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

C35H31N3O9S → 1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine (29706-84-1)

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

Conditions	Yield
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) → 1-(3-Azido-2,3-dideoxy-5-O-trityl-β-D-threo-pentofuranosyl)thymine (66503-47-7) + 1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine (29706-84-1)

Conditions	Yield
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) → 5'-O-trityl-2,3'-anhydrothymidine (25442-42-6) + 1-(3-Azido-2,3-dideoxy-5-O-trityl-β-D-threo-pentofuranosyl)thymine (66503-47-7) + 1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine (29706-84-1)

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

Conditions	Yield
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) → 6,3'-Imino-1-(2,3-dideoxy-5-O-trityl-β-D-threo-pentofuranosyl)thymine (73971-78-5) + 1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine (29706-84-1)

Conditions	Yield
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) + NaN3 → 1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine (29706-84-1)

Conditions	Yield
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-Azido-2,3-dideoxy-5-O-trityl-β-D-threo-pentofuranosyl)thymine (66503-47-7) + 1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine (29706-84-1)

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

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

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

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

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

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

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

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

Conditions	Yield
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) → 3'-azido-2',3'-deoxythymidine (30516-87-1)

Conditions	Yield
With silica gel; trifluoroacetic acid In methanol; chloroform	95%
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) → 3'-amino-3'-deoxy-5'-O-triphenylmethyl-β-D-thymidine (124355-25-5)

Conditions	Yield
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) + 1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine (29706-84-1) → C34H34N6O6

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile for 3h; Inert atmosphere; Reflux; stereoselective reaction;	91%

N,N-dimethylformamide diethyl diacetal (1188-33-6) + 1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine (29706-84-1) → 3'-azido-3'-deoxy-3-ethyl-5'-O-tritylthymidine

Conditions	Yield
In N,N-dimethyl-formamide at 100℃; for 24h;	82%

allyl bromide (106-95-6) + 1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine (29706-84-1) → 3-allyl-3'-azido-3'-deoxy-5'-O-tritylthymidine

Conditions	Yield
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) + 1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine (29706-84-1) → 4-[2-(2-fluoroethoxy)ethoxymethyl]-1-(5-O-trityl-2-deoxythymidin-3-yl)-1H-[1,2,3]triazole

Conditions	Yield
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) + 1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine (29706-84-1) → 3'-azido-3'-deoxy-3-(2-methyl-2-butenyl)-5'-O-tritylthymidine

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 60℃; for 4h;	64%

5'-O-trityl-2,3'-anhydrothymidine (25442-42-6) + 1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine (29706-84-1) → 3'-azido-2',3'-deoxythymidine (30516-87-1) + thymin (65-71-4) + 3'-N''-(3'''-azido-3'''-deoxythymid-3''-yl)-3'-deoxythymidine

Conditions	Yield
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) → 3'-amino-3'-deoxythymidine (52450-18-7)

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

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

Conditions	Yield
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) + trimethylphosphane (594-09-2) → C32H36N3O4P

Conditions	Yield
In toluene for 1h; Ambient temperature;

2-(2-(prop-2-yn-1-yloxy)ethoxy)ethyl methanesulfonate (943726-01-0) + 1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine (29706-84-1) → C36H38(18)FN5O6

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

Conditions	Yield
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) → C45H40N4O6S

Conditions	Yield
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) → [(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	Yield
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-((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)

Conditions	Yield
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

Upstream product

• 55612-11-8 5'-O-trityldeoxyxylothymidine 
• 30516-87-1 3'-azido-2',3'-deoxythymidine 
• 76-83-5 trityl chloride 
• 95585-76-5 2'-bromothymidine 
• 162404-30-0 AZT guanidine salt 
• 42214-24-4 1-(2-deoxy-3-O-methanesulfonyl-5-O-trityl-β-D-ribopentofuranosyl)thymine 
• 7791-71-1 5'-O-tritylthymidine 
• 25442-42-6 5'-O-trityl-2,3'-anhydrothymidine 
• 25442-44-8 1-(3'-iodo-2',3'-dideoxy-5'-O-trityl-β-D-erythro-pentofuranosyl)thymine 
• 104218-44-2 1-(2-deoxy-3-O-methanesulfonyl-5-O-trityl-β-D-threo-pentofuranosyl)thymine 

Downstream Products

• 141039-00-1 3'-N-methylamino-3'-deoxythymidine 
• 153907-25-6 5-Methyl-1-((2R,4S,5S)-4-methylamino-5-trityloxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione 
• 153907-27-8 1-((2R,4S,5S)-4-Ethylamino-5-trityloxymethyl-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione 
• 153907-26-7 1-((2R,4S,5S)-4-Dimethylamino-5-trityloxymethyl-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione 
• 153907-29-0 1-((2R,4S,5S)-4-Isopropylamino-5-trityloxymethyl-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione 
• 153907-30-3 1-((2R,4S,5S)-4-Allylamino-5-trityloxymethyl-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione 
• 153907-28-9 5-Methyl-1-((2R,4S,5S)-4-propylamino-5-trityloxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione 
• 153907-31-4 3'-benzylamino-3'-deoxy-5'-O-triphenylmethyl-β-D-thymidine 
• 153907-32-5 1-[(2R,4S,5S)-4-(4-Fluoro-benzylamino)-5-trityloxymethyl-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione 
• 87190-79-2 3'-azido-5-methyl-2',3'-dideoxycytidine 

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