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

Base Information

• Chemical Name: 1-[3,5-di-O-benzyl-4-C-cyanomethyl-2-O-trifluoromethanesulfonyl-β-D-arabinofuranosyl]thymine
• CAS No.: 918132-61-3
• Molecular Formula: C₂₇H₂₆F₃N₃O₈S
• Molecular Weight: 609.58
• Mol file: 918132-61-3.mol

Synonyms:1-[3,5-di-O-benzyl-4-C-cyanomethyl-2-O-trifluoromethanesulfonyl-β-D-arabinofuranosyl]thymine

Chemical Property of 1-[3,5-di-O-benzyl-4-C-cyanomethyl-2-O-trifluoromethanesulfonyl-β-D-arabinofuranosyl]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-C-cyanomethyl-2-O-trifluoromethanesulfonyl-β-D-arabinofuranosyl]thymine

There total 5 articles about 1-[3,5-di-O-benzyl-4-C-cyanomethyl-2-O-trifluoromethanesulfonyl-β-D-arabinofuranosyl]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: 84.0%

1-[3,5-di-O-benzyl-4-cyanomethyl-β-D-arabinofuranosyl]thymine (918132-59-9) + trifluoromethylsulfonic anhydride (358-23-6) → 1-[3,5-di-O-benzyl-4-C-cyanomethyl-2-O-trifluoromethanesulfonyl-β-D-arabinofuranosyl]thymine (918132-61-3)

Guidance literature:

With dmap; In pyridine; dichloromethane; at 0 ℃; for 2.5h;

DOI:10.1021/ja0634977

Reference yield:

(3-benzyloxy-2-benzyloxymethyl-7-methyl-6-oxo-2,3,3a,9a-tetrahydro-6H-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-2-yl)-acetonitrile → 1-[3,5-di-O-benzyl-4-C-cyanomethyl-2-O-trifluoromethanesulfonyl-β-D-arabinofuranosyl]thymine (918132-61-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / aq. H₂SO₄ / acetone / Heating

2: 84 percent / 4-dimethylaminopyridine / CH₂Cl₂; pyridine / 2.5 h / 0 °C

With dmap; sulfuric acid; In pyridine; dichloromethane; acetone;

DOI:10.1021/ja0634977

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) → 1-[3,5-di-O-benzyl-4-C-cyanomethyl-2-O-trifluoromethanesulfonyl-β-D-arabinofuranosyl]thymine (918132-61-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 6.2 g / pyridine / 6 h / 0 °C

2: 91 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 1 h / 20 °C

3: 100 percent / aq. H₂SO₄ / acetone / Heating

4: 84 percent / 4-dimethylaminopyridine / CH₂Cl₂; pyridine / 2.5 h / 0 °C

With pyridine; dmap; sulfuric acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In pyridine; dichloromethane; acetone; acetonitrile;

DOI:10.1021/ja0634977

upstream raw materials:

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

trifluoromethylsulfonic anhydride

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

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

Downstream raw materials:

(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

(1R,3R,4R,6S)-1-benzyloxymethyl-6-benzyloxy-5-carbonitrile-3-(thymin-1-yl)-2-oxabicyclo[2.1.1]hexane