[(1S,3R)-3-[(tert-butyldimethylsilyl)oxy]-1-hydroxy-4-methylene]cyclohexanecarboxylic acid methyl ester

Base Information

Chemical Name:[(1S,3R)-3-[(tert-butyldimethylsilyl)oxy]-1-hydroxy-4-methylene]cyclohexanecarboxylic acid methyl ester
CAS No.:1246364-46-4
Molecular Formula:C₁₅H₂₈O₄Si
Molecular Weight:300.47
Hs Code.:

Synonyms:[(1S,3R)-3-[(tert-butyldimethylsilyl)oxy]-1-hydroxy-4-methylene]cyclohexanecarboxylic acid methyl ester

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Chemical Property of [(1S,3R)-3-[(tert-butyldimethylsilyl)oxy]-1-hydroxy-4-methylene]cyclohexanecarboxylic acid methyl ester

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Technology Process of [(1S,3R)-3-[(tert-butyldimethylsilyl)oxy]-1-hydroxy-4-methylene]cyclohexanecarboxylic acid methyl ester

There total 12 articles about [(1S,3R)-3-[(tert-butyldimethylsilyl)oxy]-1-hydroxy-4-methylene]cyclohexanecarboxylic acid methyl ester 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: 80.0%

: 67-56-1
methanol

: 1246364-44-2
(1S,5R)-1-Hydroxy-4-methylene-6-oxa-bicyclo[3.2.1]octan-7-one

: 69739-34-0
t-butyldimethylsiyl triflate

: 1246364-46-4
[(1S,3R)-3-[(tert-butyldimethylsilyl)oxy]-1-hydroxy-4-methylene]cyclohexanecarboxylic acid methyl ester

Guidance literature:: methanol; (1S,5R)-1-Hydroxy-4-methylene-6-oxa-bicyclo[3.2.1]octan-7-one; at 20 ℃; for 48h; Molecular sieve;

t-butyldimethylsiyl triflate; With 2,6-dimethylpyridine; In dichloromethane; at -40 - 20 ℃;

Reference yield:

: C₈H₈O₆S

: 1246364-46-4
[(1S,3R)-3-[(tert-butyldimethylsilyl)oxy]-1-hydroxy-4-methylene]cyclohexanecarboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / tetrahydrofuran; benzene

2: dipyridinium dichromate / acetonitrile / Molecular sieve

3: potassium tert-butylate / tetrahydrofuran

4: Molecular sieve

5: 2,6-dimethylpyridine / dichloromethane

With 2,6-dimethylpyridine; dipyridinium dichromate; 2,2'-azobis(isobutyronitrile); potassium tert-butylate; tri-n-butyl-tin hydride; In tetrahydrofuran; dichloromethane; acetonitrile; benzene; 1: Barton-McCombie deoxygenation / 3: Wittig reaction;
DOI:10.1016/j.jsbmb.2010.03.063

Reference yield:

: C₇H₁₀O₅

: 1246364-46-4
[(1S,3R)-3-[(tert-butyldimethylsilyl)oxy]-1-hydroxy-4-methylene]cyclohexanecarboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: dipyridinium dichromate / acetonitrile / Molecular sieve

2: potassium tert-butylate / tetrahydrofuran

3: Molecular sieve

4: 2,6-dimethylpyridine / dichloromethane

With 2,6-dimethylpyridine; dipyridinium dichromate; potassium tert-butylate; In tetrahydrofuran; dichloromethane; acetonitrile; 2: Wittig reaction;
DOI:10.1016/j.jsbmb.2010.03.063