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

Base Information

• Chemical Name: (1R,2S,5R,7R,8S)-5-benzyloxymethyl-8-benzyloxy-7-(thymin-1-yl)-2-aza-6-oxabicyclo[3.2.1]octane
• CAS No.: 939017-19-3
• Molecular Formula: C₂₆H₂₉N₃O₅
• Molecular Weight: 463.533
• Mol file: 939017-19-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 14 articles about (1R,2S,5R,7R,8S)-5-benzyloxymethyl-8-benzyloxy-7-(thymin-1-yl)-2-aza-6-oxabicyclo[3.2.1]octane 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: 40.0%

1-[3,5-di-O-benzyl-4-C-cyanomethyl-2-O-trifluoromethanesulfonyl-β-D-arabinofuranosyl]thymine (918132-61-3) → (1R,2R,5R,7R,8S)-5-benzyloxymethyl-8-benzyloxy-7-(thymin-1-yl)-2-aza-6-oxabicyclo[3.2.1]octane (939017-19-3) + (1R,2S,5R,7R,8S)-5-benzyloxymethyl-8-benzyloxy-7-(thymin-1-yl)-2-aza-6-oxabicyclo[3.2.1]octane (939017-19-3)

Guidance literature:

With sodium tetrahydroborate; trifluoroacetic acid; In tetrahydrofuran; at 20 ℃;

DOI:10.1021/ja0634977

Reference yield: 40.0%

1-[3,5-di-O-benzyl-4-C-cyanomethyl-2-O-trifluoromethanesulfonyl-β-D-arabinofuranosyl]thymine (918132-61-3) → (1R,2R,5R,7R,8S)-5-benzyloxymethyl-8-benzyloxy-7-(thymin-1-yl)-2-aza-6-oxabicyclo[3.2.1]octane (939017-19-3) + (1R,2S,5R,7R,8S)-5-benzyloxymethyl-8-benzyloxy-7-(thymin-1-yl)-2-aza-6-oxabicyclo[3.2.1]octane (939017-19-3)

Guidance literature:

With sodium tetrahydroborate; trifluoroacetic acid; In tetrahydrofuran; at 20 ℃;

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 → (1R,2R,5R,7R,8S)-5-benzyloxymethyl-8-benzyloxy-7-(thymin-1-yl)-2-aza-6-oxabicyclo[3.2.1]octane (939017-19-3)

Guidance literature:

Multi-step reaction with 3 steps

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

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

3: 5 percent / NaBH₄; trifluoroacetic acid / tetrahydrofuran / 20 °C

With dmap; sodium tetrahydroborate; sulfuric acid; trifluoroacetic acid; In tetrahydrofuran; pyridine; dichloromethane; acetone;

DOI:10.1021/ja0634977

upstream raw materials:

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

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

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