1-[2-azido-3-O-benzyl-2-deoxy-5-O-methanesulfonyl-4-C-(methanesulfonyloxymethyl)-β-D-erythro-pentofuranosyl]thymine

Base Information

• Chemical Name: 1-[2-azido-3-O-benzyl-2-deoxy-5-O-methanesulfonyl-4-C-(methanesulfonyloxymethyl)-β-D-erythro-pentofuranosyl]thymine
• CAS No.: 552856-41-4
• Molecular Formula: C₂₀H₂₅N₅O₁₀S₂
• Molecular Weight: 559.578
• Mol file: 552856-41-4.mol

Synonyms:1-[2-azido-3-O-benzyl-2-deoxy-5-O-methanesulfonyl-4-C-(methanesulfonyloxymethyl)-β-D-erythro-pentofuranosyl]thymine

Chemical Property of 1-[2-azido-3-O-benzyl-2-deoxy-5-O-methanesulfonyl-4-C-(methanesulfonyloxymethyl)-β-D-erythro-pentofuranosyl]thymine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[2-azido-3-O-benzyl-2-deoxy-5-O-methanesulfonyl-4-C-(methanesulfonyloxymethyl)-β-D-erythro-pentofuranosyl]thymine

There total 28 articles about 1-[2-azido-3-O-benzyl-2-deoxy-5-O-methanesulfonyl-4-C-(methanesulfonyloxymethyl)-β-D-erythro-pentofuranosyl]thymine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.0%

1-(3-O-benzyl-5-O-methanesulfonyl-4-C-methanesulfonyloxymethyl-2-O-trifluoromethanesulfonyl-β-D-threo-pentofuranosyl)-thymine (552856-40-3) → 1-[2-azido-3-O-benzyl-2-deoxy-5-O-methanesulfonyl-4-C-(methanesulfonyloxymethyl)-β-D-erythro-pentofuranosyl]thymine (552856-41-4)

Guidance literature:

With sodium azide; 15-crown-5; In N,N-dimethyl-formamide;

DOI:10.1081/NCN-120022818

Reference yield: 91.0%

1-(3-O-benzyl-5-O-methanesulfonyl-4-C-methanesulfonyloxymethyl-β-D-threo-pentofuranosyl)thymine (552856-39-0) → 1-[2-azido-3-O-benzyl-2-deoxy-5-O-methanesulfonyl-4-C-(methanesulfonyloxymethyl)-β-D-erythro-pentofuranosyl]thymine (552856-41-4)

Guidance literature:

1-(3-O-benzyl-5-O-methanesulfonyl-4-C-methanesulfonyloxymethyl-β-D-threo-pentofuranosyl)thymine; With dmap; trifluoromethylsulfonic anhydride; In pyridine; dichloromethane; at 0 ℃; for 2h;

With sodium azide; In DMF (N,N-dimethyl-formamide); at 20 ℃; for 4h;

Reference yield: 48.0%

1-(3-O-benzyl-5-O-methanesulfonyl-4-C-methanesulfonyloxymethyl-β-D-threo-pentofuranosyl)thymine (552856-39-0) → 1-(5-O-methanesulfonyl-4-C-methanesulfonyloxymethyl-3-O-benzyl-2-deoxy-2-azido-β-D-erythro-pentofuranosyl)-4-azido-5-methylpyrimidin-2(1H)-one (1415236-69-9) + 1-[2-azido-3-O-benzyl-2-deoxy-5-O-methanesulfonyl-4-C-(methanesulfonyloxymethyl)-β-D-erythro-pentofuranosyl]thymine (552856-41-4)

Guidance literature:

1-(3-O-benzyl-5-O-methanesulfonyl-4-C-methanesulfonyloxymethyl-β-D-threo-pentofuranosyl)thymine; With pyridine; dmap; trifluoromethylsulfonic anhydride; In dichloromethane; at 0 ℃; for 2h; Inert atmosphere;

With sodium azide; 15-crown-5; In N,N-dimethyl-formamide; at 80 ℃; for 19h; Inert atmosphere;

DOI:10.1021/jo302036h

upstream raw materials:

1-(3-O-benzyl-5-O-methanesulfonyl-4-C-methanesulfonyloxymethyl-2-O-trifluoromethanesulfonyl-β-D-threo-pentofuranosyl)-thymine

methanesulfonyl chloride

1-(3-O-benzyl-5-O-methanesulfonyl-4-C-methanesulfonyloxymethyl-β-D-erythro-pentofuranosyl)thymine

1-(3-O-benzyl-2,5-di-O-methanesulfonyl-4-C-(methanesulfonyloxymethyl)-β-D-erythro-pentofuranosyl)thymine

Downstream raw materials:

(1R,3R,4R,7S)-7-benzyloxy-1-methanesulfonyloxymethyl-3-(thymin-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane

[3-(6-amino-purin-9-yl)-7-benzyloxy-2-oxa-5-aza-bicyclo[2.2.1]hept-1-yl]-methanol

methanesulfonic acid 3-(2-amino-6-chloro-purin-9-yl)-7-benzyloxy-2-oxa-5-aza-bicyclo[2.2.1]hept-1-ylmethyl ester

[3-(2-amino-6-benzyloxy-purin-9-yl)-7-benzyloxy-2-oxa-5-aza-bicyclo[2.2.1]hept-1-yl]-methanol