1-[3,5-di-O-benzyl-4-cyanomethyl-2-O-methanesulfonyl-β-D-ribofuranosyl]thymine

Base Information

• Chemical Name: 1-[3,5-di-O-benzyl-4-cyanomethyl-2-O-methanesulfonyl-β-D-ribofuranosyl]thymine
• CAS No.: 918132-56-6
• Molecular Formula: C₂₇H₂₉N₃O₈S
• Molecular Weight: 555.609

Synonyms:1-[3,5-di-O-benzyl-4-cyanomethyl-2-O-methanesulfonyl-β-D-ribofuranosyl]thymine

Chemical Property of 1-[3,5-di-O-benzyl-4-cyanomethyl-2-O-methanesulfonyl-β-D-ribofuranosyl]thymine

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[3,5-di-O-benzyl-4-cyanomethyl-2-O-methanesulfonyl-β-D-ribofuranosyl]thymine

There total 2 articles about 1-[3,5-di-O-benzyl-4-cyanomethyl-2-O-methanesulfonyl-β-D-ribofuranosyl]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:

2-((2R,3S,4R,5R)-3-(benzyloxy)-2-((benzyloxy)methyl)-4-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)acetonitrile (938193-16-9) + methanesulfonyl chloride (124-63-0) → 1-[3,5-di-O-benzyl-4-cyanomethyl-2-O-methanesulfonyl-β-D-ribofuranosyl]thymine (918132-56-6)

Guidance literature:

With pyridine; at 0 ℃; for 6h;

DOI:10.1021/ja0634977

Reference yield:

1-[2-O-acetyl-3,5-di-O-benzyl-4-C-cyanomethyl-β-D-ribofuranosyl]thymine (918132-54-4) → 1-[3,5-di-O-benzyl-4-cyanomethyl-2-O-methanesulfonyl-β-D-ribofuranosyl]thymine (918132-56-6)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium methoxide / methanol / 3 h / 20 °C

2: 6.2 g / pyridine / 6 h / 0 °C

With pyridine; sodium methylate; In methanol;

DOI:10.1021/ja0634977

Reference yield: 91.0%

1-[3,5-di-O-benzyl-4-cyanomethyl-2-O-methanesulfonyl-β-D-ribofuranosyl]thymine (918132-56-6) → 2,2'-anhydro-1-[3,5-di-O-benzyl-4-C-cyanomethyl-β-D-ribofuranosyl]thymine (918132-57-7)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; at 20 ℃; for 1h;

upstream raw materials:

2-((2R,3S,4R,5R)-3-(benzyloxy)-2-((benzyloxy)methyl)-4-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)acetonitrile

methanesulfonyl chloride

1-[2-O-acetyl-3,5-di-O-benzyl-4-C-cyanomethyl-β-D-ribofuranosyl]thymine

Downstream raw materials:

2,2'-anhydro-1-[3,5-di-O-benzyl-4-C-cyanomethyl-β-D-ribofuranosyl]thymine

(1R,2R,5R,7R,8S)-5-benzyloxymethyl-8-benzyloxy-7-(thymin-1-yl)-2-aza-6-oxabicyclo[3.2.1]octane

(1R,2S,5R,7R,8S)-5-benzyloxymethyl-8-benzyloxy-7-(thymin-1-yl)-2-aza-6-oxabicyclo[3.2.1]octane

1-[3,5-di-O-benzyl-4-cyanomethyl-β-D-arabinofuranosyl]thymine

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