Name: 3-Azido-3-deoxy-5-O-triphenylmethylthymidine
SKU: 29706-84-1

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Pharmaceutical (48)
Others (8)
Organic Chemicals (8)

Basic Information

Molecular Structure:
CAS No.:	29706-84-1
Name:	3-Azido-3-deoxy-5-O-triphenylmethylthymidine
Article Data:	13

Formula:	C29H27 N5 O4
Molecular Weight:	509.564
Synonyms:	Thymidine,3'-azido-3'-deoxy-5'-O-trityl- (8CI); 3'-Azido-3'-deoxy-5'-O-tritylthymidine
Melting Point:	103-104 °C(Solv: toluene (108-88-3))
PSA:	123.33000
LogP:	4.68516

Synthetic route

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

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

Conditions

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

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

: 76-83-5
trityl chloride

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

Conditions

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

: C35H31N3O9S

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

Conditions

Conditions	Yield
With sodium azide In N,N-dimethyl-formamide at 20℃; for 24h;	94%

: 104218-44-2
1-(2-deoxy-3-O-methanesulfonyl-5-O-trityl-β-D-threo-pentofuranosyl)thymine

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

Conditions

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;

: 55612-11-8
5'-O-trityldeoxyxylothymidine

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

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

Conditions

Conditions	Yield
With lithium azide; carbon tetrabromide; triphenylphosphine In N,N-dimethyl-formamide for 43h; Ambient temperature;	A n/a B 67%

: 42214-24-4
1-(2-deoxy-3-O-methanesulfonyl-5-O-trityl-β-D-ribopentofuranosyl)thymine

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

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

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

Conditions

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%

...Expand

: 7791-71-1
5'-O-tritylthymidine

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

Conditions

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

: 42214-24-4
1-(2-deoxy-3-O-methanesulfonyl-5-O-trityl-β-D-ribopentofuranosyl)thymine

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

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

Conditions

Conditions	Yield
With sodium azide In N,N-dimethyl-formamide for 24h; Heating;	A 43% B 41%

: 42214-24-4
1-(2-deoxy-3-O-methanesulfonyl-5-O-trityl-β-D-ribopentofuranosyl)thymine

NaN3: NaN3

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

Conditions

Conditions	Yield
In N,N-dimethyl-formamide for 24h; Heating;	43%

: 25442-44-8
1-(3'-iodo-2',3'-dideoxy-5'-O-trityl-β-D-erythro-pentofuranosyl)thymine

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

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

Conditions

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;