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

Base Information

• Chemical Name: 6-[(2S,3R)-3-Hydroxy-2-((E)-(3S,5S)-3-hydroxy-5-methyl-non-1-enyl)-5-oxo-cyclopentylsulfanyl]-hexanoic acid methyl ester
• CAS No.: 83010-01-9
• Molecular Formula: C₂₂H₃₈O₅S
• Molecular Weight: 414.607
• Mol file: 83010-01-9.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 14 articles about 6-[(2S,3R)-3-Hydroxy-2-((E)-(3S,5S)-3-hydroxy-5-methyl-non-1-enyl)-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: 92.0%

6-{(1R,2S,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(3S,5R)-3-(tert-butyl-dimethyl-silanyloxy)-5-methyl-non-1-enyl]-5-oxo-cyclopentylsulfanyl}-hexanoic acid methyl ester (83058-57-5) → 17(R),20-dimethyl-7-thiaprostaglandin E1 methyl ester (83010-01-9,83058-69-9,99295-31-5,122405-22-5)

Guidance literature:

With pyridine; hydrogen fluoride; In acetonitrile; for 2h;

DOI:10.1248/cpb.33.2359

Reference yield: 80.0%

6-{(1R,2S,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(3S,5S)-3-(tert-butyl-dimethyl-silanyloxy)-5-methyl-non-1-enyl]-5-oxo-cyclopentylsulfanyl}-hexanoic acid methyl ester (83009-73-8) → 6-[(2S,3R)-3-Hydroxy-2-((E)-(3S,5S)-3-hydroxy-5-methyl-non-1-enyl)-5-oxo-cyclopentylsulfanyl]-hexanoic acid methyl ester (83010-01-9,83058-69-9,99295-31-5,122405-22-5)

Guidance literature:

With hydrogen fluoride; In acetonitrile;

DOI:10.1248/cpb.33.2359

Reference yield:

1-mercapto-5-carbomethoxy-pentane (20756-86-9) → 17(R),20-dimethyl-7-thiaprostaglandin E1 methyl ester (83010-01-9,83058-69-9,99295-31-5,122405-22-5)

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: 92 percent / HF, pyridine / acetonitrile / 2 h

With pyridine; hydrogen fluoride; tert.-butyl lithium; copper(I) thiophenolate; triethylamine; Hexamethylphosphorous triamide; In methanol; acetonitrile;

DOI:10.1248/cpb.33.2359

upstream raw materials:

6-{(1R,2S,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(3S,5R)-3-(tert-butyl-dimethyl-silanyloxy)-5-methyl-non-1-enyl]-5-oxo-cyclopentylsulfanyl}-hexanoic acid methyl ester

1-mercapto-5-carbomethoxy-pentane

methyl-6-<(4R)-tert-butyldimethylsilyloxy-2-oxo-5-cyclopenten-1-ylthio>hexanoate

(1E,3S,5R)-1-iodo-3-(tert-butyldimethylsiloxy)-5-methyl-1-nonene