(1R,3R,4R,7S)-7-benzyloxy-1-methanesulfonyloxymethyl-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-methanesulfonyloxymethyl-5-methyl-3-(thymin-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane
CAS No.:625111-32-2
Molecular Formula:C₂₀H₂₅N₃O₇S
Molecular Weight:451.5
Hs Code.:

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

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

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

There total 20 articles about (1R,3R,4R,7S)-7-benzyloxy-1-methanesulfonyloxymethyl-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: 90.0%

: 50-00-0,30525-89-4,61233-19-0
formaldehyd

: 552856-42-5
(1R,3R,4R,7S)-7-benzyloxy-1-methanesulfonyloxymethyl-3-(thymin-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane

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

Guidance literature:: With formic acid;
DOI:10.1081/NCN-120022818

Reference yield:

: 293751-04-9
1-(2-O-acetyl-3-O-benzyl-4-C-methanesulfonyloxymethyl-5-O-methanesulfonyl-β-D-erythro-pentofuranosyl)thymine

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

Guidance literature:: Multi-step reaction with 8 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

With pyridine; dmap; sodium hydroxide; formic acid; 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; 8: Eschweiler-Clarke reaction;
DOI:10.1081/NCN-120022818

Reference yield:

: 552856-38-9
2,2'-anhydro-1-(3-O-benzyl-5-O-methanesulfonyl-4-C-methanesulfonyloxymethyl-β-D-threo-pentofuranosyl)thymine

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

Guidance literature:: Multi-step reaction with 5 steps

1: 98 percent / sulfuric acid / H₂O; acetone / Heating

2: 80 percent / 4-(dimethylamino)pyridine; pyridine / CH₂Cl₂ / 0 °C

3: 91 percent / sodium azide; 15-croen-5 / dimethylformamide

4: 93 percent / trimethylphosphine; NaOH / H₂O; tetrahydrofuran

5: 90 percent / HCO₂H

With pyridine; dmap; sodium hydroxide; formic acid; sodium azide; 15-crown-5; sulfuric acid; trimethylphosphane; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone; 5: Eschweiler-Clarke reaction;
DOI:10.1081/NCN-120022818