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

Base Information

• Chemical Name: (1R,3R,4R,7S)-7-benzyloxy-1-methanesulfonyloxymethyl-3-(thymin-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane
• CAS No.: 552856-42-5
• Molecular Formula: C₁₉H₂₃N₃O₇S
• Molecular Weight: 437.474
• Mol file: 552856-42-5.mol

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

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

There total 23 articles about (1R,3R,4R,7S)-7-benzyloxy-1-methanesulfonyloxymethyl-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: 93.0%

1-[2-azido-3-O-benzyl-2-deoxy-5-O-methanesulfonyl-4-C-(methanesulfonyloxymethyl)-β-D-erythro-pentofuranosyl]thymine (552856-41-4) → (1R,3R,4R,7S)-7-benzyloxy-1-methanesulfonyloxymethyl-3-(thymin-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane (552856-42-5)

Guidance literature:

With sodium hydroxide; trimethylphosphane; In tetrahydrofuran; water;

DOI:10.1081/NCN-120022818

Reference yield:

1-(3-O-benzyl-5-O-methanesulfonyl-4-C-methanesulfonyloxymethyl-β-D-erythro-pentofuranosyl)thymine (293751-06-1) → (1R,3R,4R,7S)-7-benzyloxy-1-methanesulfonyloxymethyl-3-(thymin-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane (552856-42-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 93 percent / pyridine

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

3: 98 percent / sulfuric acid / H₂O; acetone / Heating

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

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

6: 93 percent / trimethylphosphine; NaOH / H₂O; tetrahydrofuran

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

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-methanesulfonyloxymethyl-3-(thymin-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane (552856-42-5)

Guidance literature:

Multi-step reaction with 7 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

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

DOI:10.1081/NCN-120022818

upstream raw materials:

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

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

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

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

Downstream raw materials:

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

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

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

(1R,3R,4R,7S)-7-benzyloxy-1-(4,4'-dimethoxytrityl)oxymethyl-3-(4-N-benzoyl-5-methylcytosin-1-yl)-5-trifluoroacetyl-2-oxa-5-azabicyclo[2.2.1]heptane