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

Base Information

• Chemical Name: (1R,3R,4R,7S)-7-benzyloxy-1-hydroxymethyl-5-methyl-3-(thymin-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane
• CAS No.: 552856-48-1
• Molecular Formula: C₁₉H₂₃N₃O₅
• Molecular Weight: 373.409
• Mol file: 552856-48-1.mol

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

Chemical Property of (1R,3R,4R,7S)-7-benzyloxy-1-hydroxymethyl-5-methyl-3-(thymin-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,3R,4R,7S)-7-benzyloxy-1-hydroxymethyl-5-methyl-3-(thymin-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane

There total 22 articles about (1R,3R,4R,7S)-7-benzyloxy-1-hydroxymethyl-5-methyl-3-(thymin-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane 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: 98.0%

(1R,3R,4R,7S)-7-benzyloxy-1-methanesulfonyloxymethyl-5-methyl-3-(thymin-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane (625111-32-2) → (1R,3R,4R,7S)-7-benzyloxy-1-hydroxymethyl-5-methyl-3-(thymin-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane (552856-48-1)

Guidance literature:

With sodium benzoate; sodium methylate; In DMF (N,N-dimethyl-formamide); dichloromethane; at 100 ℃; for 8h;

Reference yield:

Benzoic acid (1R,3R,4R,7S)-7-benzyloxy-5-methyl-3-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-oxa-5-aza-bicyclo[2.2.1]hept-1-ylmethyl ester → (1R,3R,4R,7S)-7-benzyloxy-1-hydroxymethyl-5-methyl-3-(thymin-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane (552856-48-1)

Guidance literature:

With sodium methylate; In N,N-dimethyl-formamide;

DOI:10.1081/NCN-120022818

Reference yield:

1-(2-O-acetyl-3-O-benzyl-4-C-methanesulfonyloxymethyl-5-O-methanesulfonyl-β-D-erythro-pentofuranosyl)thymine (293751-04-9) → (1R,3R,4R,7S)-7-benzyloxy-1-hydroxymethyl-5-methyl-3-(thymin-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane (552856-48-1)

Guidance literature:

Multi-step reaction with 10 steps

1: 97 percent / NH₃ / methanol

2: 93 percent / pyridine

3: 91 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile

4: 98 percent / sulfuric acid / H₂O; acetone / Heating

5: 80 percent / 4-(dimethylamino)pyridine; pyridine / CH₂Cl₂ / 0 °C

6: 91 percent / sodium azide; 15-croen-5 / dimethylformamide

7: 93 percent / trimethylphosphine; NaOH / H₂O; tetrahydrofuran

8: 90 percent / HCO₂H

9: sodium methoxide / dimethylformamide

With pyridine; dmap; sodium hydroxide; formic acid; sodium azide; 15-crown-5; sulfuric acid; ammonia; sodium methylate; 1,8-diazabicyclo[5.4.0]undec-7-ene; trimethylphosphane; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile; 8: Eschweiler-Clarke reaction;

DOI:10.1081/NCN-120022818

upstream raw materials:

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

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

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

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