Cpt-PGE1

Base Information

• Chemical Name: Cpt-PGE1
• CAS No.: 83009-96-5
• Molecular Formula: C₂₁H₃₄O₅S
• Molecular Weight: 398.564
• Mol file: 83009-96-5.mol

Synonyms:15-cyclohexyl-omega-pentanor-7-thiaprostaglandin E1;CPT-PGE1

Chemical Property of Cpt-PGE1

Chemical Property:

• Vapor Pressure: 5.07E-14mmHg at 25°C
• Boiling Point: 542.3°C at 760 mmHg
• Flash Point: 281.8°C
• PSA: 109.13000
• Density: 1.16g/cm³
• LogP: 3.26890
• XLogP3: 3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 11
• Exact Mass: 398.21269535
• Heavy Atom Count: 27
• Complexity: 501

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)CCCCCSC1C(C(CC1=O)O)C=CC(C2CCCCC2)O
• Isomeric SMILES: COC(=O)CCCCCS[C@@H]1[C@H]([C@@H](CC1=O)O)/C=C/C(C2CCCCC2)O

Technology Process of Cpt-PGE1

There total 8 articles about Cpt-PGE1 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: 76.0%

6-{(1R,2S,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-3-cyclohexyl-propenyl]-5-oxo-cyclopentylsulfanyl}-hexanoic acid methyl ester (83009-66-9) → 15-cyclohexyl-w-pentanor-7-thiaprostaglandin E1 methyl ester (83009-96-5,83058-68-8,99295-30-4)

Guidance literature:

With hydrogen fluoride; In acetonitrile;

DOI:10.1248/cpb.33.2359

Reference yield:

3-cyclohexyl-3RS-hydroxy-1-iodoprop-1E-ene (71399-48-9) → 15-cyclohexyl-w-pentanor-7-thiaprostaglandin E1 methyl ester (83009-96-5,83058-68-8,99295-30-4)

Guidance literature:

Multi-step reaction with 4 steps

2: 99 percent

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

4: 76 percent / 47 percent aq. HF / acetonitrile

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

DOI:10.1248/cpb.33.2359

Reference yield:

1-mercapto-5-carbomethoxy-pentane (20756-86-9) → 15-cyclohexyl-w-pentanor-7-thiaprostaglandin E1 methyl ester (83009-96-5,83058-68-8,99295-30-4)

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: 76 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

upstream raw materials:

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

3-cyclohexyl-3RS-hydroxy-1-iodoprop-1E-ene

1-mercapto-5-carbomethoxy-pentane

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

Downstream raw materials:

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

15-cyclohexyl-ω-pentanor-7-thiaprostaglandin E₁

6-[(1R,2S,3R)-2-((E)-(S)-3-Cyclohexyl-3-hydroxy-propenyl)-3-hydroxy-5-oxo-cyclopentanesulfinyl]-hexanoic acid methyl ester

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