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

Base Information

Chemical Name:(1S,3R,4S,7R)-7-benzyloxy-1-hydroxymethyl-3-(thymin-1-yl)-5-trifluoroacetyl-2-oxa-5-azabicyclo[2.2.1]heptane
CAS No.:894430-44-5
Molecular Formula:C₂₀H₂₀F₃N₃O₆
Molecular Weight:455.391
Hs Code.:

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

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

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

There total 11 articles about (1S,3R,4S,7R)-7-benzyloxy-1-hydroxymethyl-3-(thymin-1-yl)-5-trifluoroacetyl-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: 70.0%

: 894430-43-4
(1S,3R,4S,7R)-7-benzyloxy-1-methanesulfonoxymethyl-3-(thymin-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane

: 407-25-0
trifluoroacetic anhydride

: 894430-44-5
(1S,3R,4S,7R)-7-benzyloxy-1-hydroxymethyl-3-(thymin-1-yl)-5-trifluoroacetyl-2-oxa-5-azabicyclo[2.2.1]heptane

Guidance literature:: (1S,3R,4S,7R)-7-benzyloxy-1-methanesulfonoxymethyl-3-(thymin-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane; trifluoroacetic anhydride; With pyridine; In dichloromethane;

With 18-crown-6 ether; potassium acetate; In 1,4-dioxane;

With ammonia; In methanol;
DOI:10.1080/15257770500276866

Reference yield:

: 894430-61-6
Acetic acid (1S,3R,4S,7R)-7-benzyloxy-3-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5-(2,2,2-trifluoro-acetyl)-2-oxa-5-aza-bicyclo[2.2.1]hept-1-ylmethyl ester

: 894430-44-5
(1S,3R,4S,7R)-7-benzyloxy-1-hydroxymethyl-3-(thymin-1-yl)-5-trifluoroacetyl-2-oxa-5-azabicyclo[2.2.1]heptane

Guidance literature:: With ammonia; In methanol; at 20 ℃; for 15h;
DOI:10.1021/jo060331f

Reference yield:

: 1-[2-azido-3-O-benzyl-2-deoxy-5-O-methanesulfonyl-4-C-methanesulfonoxymethyl-L-erythro-pentofuranosyl]thymine

: 894430-44-5
(1S,3R,4S,7R)-7-benzyloxy-1-hydroxymethyl-3-(thymin-1-yl)-5-trifluoroacetyl-2-oxa-5-azabicyclo[2.2.1]heptane

Guidance literature:: Multi-step reaction with 2 steps

1.1: P(CH₃)3; NaOH / tetrahydrofuran; H₂O

2.1: pyridine / CH₂Cl₂

2.2: KOAc; 18-C-6 / dioxane

2.3: 70 percent / NH₃ / methanol

With pyridine; sodium hydroxide; trimethylphosphane; In tetrahydrofuran; dichloromethane; water;
DOI:10.1080/15257770500276866