6-[(2S,3R)-2-((E)-(S)-4-Cyclohexyl-3-hydroxy-but-1-enyl)-3-hydroxy-5-oxo-cyclopentylsulfanyl]-hexanoic acid methyl ester

Base Information

Chemical Name:6-[(2S,3R)-2-((E)-(S)-4-Cyclohexyl-3-hydroxy-but-1-enyl)-3-hydroxy-5-oxo-cyclopentylsulfanyl]-hexanoic acid methyl ester
CAS No.:99234-57-8
Molecular Formula:C₂₂H₃₆O₅S
Molecular Weight:412.591
Hs Code.:

Synonyms:6-[(2S,3R)-2-((E)-(S)-4-Cyclohexyl-3-hydroxy-but-1-enyl)-3-hydroxy-5-oxo-cyclopentylsulfanyl]-hexanoic acid methyl ester

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Chemical Property of 6-[(2S,3R)-2-((E)-(S)-4-Cyclohexyl-3-hydroxy-but-1-enyl)-3-hydroxy-5-oxo-cyclopentylsulfanyl]-hexanoic acid methyl ester

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Technology Process of 6-[(2S,3R)-2-((E)-(S)-4-Cyclohexyl-3-hydroxy-but-1-enyl)-3-hydroxy-5-oxo-cyclopentylsulfanyl]-hexanoic acid methyl ester

There total 8 articles about 6-[(2S,3R)-2-((E)-(S)-4-Cyclohexyl-3-hydroxy-but-1-enyl)-3-hydroxy-5-oxo-cyclopentylsulfanyl]-hexanoic 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: 75.0%

: 99234-56-7
6-{(1R,2S,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-4-cyclohexyl-but-1-enyl]-5-oxo-cyclopentylsulfanyl}-hexanoic acid methyl ester

: 99234-57-8
6-[(2S,3R)-2-((E)-(S)-4-Cyclohexyl-3-hydroxy-but-1-enyl)-3-hydroxy-5-oxo-cyclopentylsulfanyl]-hexanoic acid methyl ester

Guidance literature:: With hydrogen fluoride; In acetonitrile;
DOI:10.1248/cpb.33.2359

Reference yield:

: 20756-86-9
1-mercapto-5-carbomethoxy-pentane

: 99234-57-8
6-[(2S,3R)-2-((E)-(S)-4-Cyclohexyl-3-hydroxy-but-1-enyl)-3-hydroxy-5-oxo-cyclopentylsulfanyl]-hexanoic acid methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 70 percent / triethylamine / methanol / 3 h / Ambient temperature

2: 1.) 2.0 M tert-BuLi, phenylthiocopper, (Me₂N)3P / 1.) pentane, ether; 2.) pentane, THF, ether

3: 75 percent / 47 percent aq. HF / acetonitrile

With hydrogen fluoride; tert.-butyl lithium; copper(I) thiophenolate; triethylamine; Hexamethylphosphorous triamide; In methanol; acetonitrile;
DOI:10.1248/cpb.33.2359

Reference yield:

: 99222-87-4
(E)-4-Chloro-1-cyclohexyl-but-3-en-2-one

: 99234-57-8
6-[(2S,3R)-2-((E)-(S)-4-Cyclohexyl-3-hydroxy-but-1-enyl)-3-hydroxy-5-oxo-cyclopentylsulfanyl]-hexanoic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 98 percent / NaI

2: 1.) (S)-BINAL-H; 2.) imidazole / 1.) THF, -100 deg C, 2 h, -78 deg C, 1 h; 2.) DMF, 2 h, RT

3: 1.) 2.0 M tert-BuLi, phenylthiocopper, (Me₂N)3P / 1.) pentane, ether; 2.) pentane, THF, ether

4: 75 percent / 47 percent aq. HF / acetonitrile

With 1H-imidazole; (-)-(S)-BINAL-H; hydrogen fluoride; tert.-butyl lithium; copper(I) thiophenolate; sodium iodide; Hexamethylphosphorous triamide; In acetonitrile;
DOI:10.1248/cpb.33.2359