(7-((1R,2R,3R)-3-(tert-butyldimethylsilyloxy)-2-(4,4-difluoro-3-oxooctyl)-5-oxocyclopentyl)heptanoic acid)

Base Information

• Chemical Name: (7-((1R,2R,3R)-3-(tert-butyldimethylsilyloxy)-2-(4,4-difluoro-3-oxooctyl)-5-oxocyclopentyl)heptanoic acid)
• CAS No.: 1372609-16-9
• Molecular Formula: C₂₆H₄₆F₂O₅Si
• Molecular Weight: 504.731
• Mol file: 1372609-16-9.mol

Synonyms:(7-((1R,2R,3R)-3-(tert-butyldimethylsilyloxy)-2-(4,4-difluoro-3-oxooctyl)-5-oxocyclopentyl)heptanoic acid)

Chemical Property of (7-((1R,2R,3R)-3-(tert-butyldimethylsilyloxy)-2-(4,4-difluoro-3-oxooctyl)-5-oxocyclopentyl)heptanoic acid)

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (7-((1R,2R,3R)-3-(tert-butyldimethylsilyloxy)-2-(4,4-difluoro-3-oxooctyl)-5-oxocyclopentyl)heptanoic acid)

There total 1 articles about (7-((1R,2R,3R)-3-(tert-butyldimethylsilyloxy)-2-(4,4-difluoro-3-oxooctyl)-5-oxocyclopentyl)heptanoic acid) 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:

(Z)-7-[(3R)-3-(tert-butyldimethylsilanyloxy)-5-oxo-cyclopent-1-enyl]hept-5-enoic acid isopropyl ester (474944-36-0) → (7-((1R,2R,3R)-3-(tert-butyldimethylsilyloxy)-2-(4,4-difluoro-3-oxooctyl)-5-oxocyclopentyl)heptanoic acid) (1372609-16-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: methyllithium / formaldehyde diethyl acetal; tetrahydrofuran / -70 - -60 °C / Inert atmosphere

1.2: 0.5 h / -50 - -40 °C / Inert atmosphere

1.3: -60 - -50 °C / Inert atmosphere

2.1: hydrogen / palladium 10% on activated carbon / ethyl acetate; water / 60 °C / 3000.3 Torr

3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -70 - -60 °C

3.2: -70 - 0 °C

4.1: sodium hydroxide; sodium dihydrogenphosphate / Lipase PS SD / acetone / 50 °C / pH 7 / Enzymatic reaction

With sodium dihydrogenphosphate; oxalyl dichloride; methyllithium; hydrogen; dimethyl sulfoxide; sodium hydroxide; palladium 10% on activated carbon; In tetrahydrofuran; formaldehyde diethyl acetal; dichloromethane; water; ethyl acetate; acetone;

Reference yield: 91.0%

(7-((1R,2R,3R)-3-(tert-butyldimethylsilyloxy)-2-(4,4-difluoro-3-oxooctyl)-5-oxocyclopentyl)heptanoic acid) (1372609-16-9) → lubiprostone (333963-40-9)

Guidance literature:

With pyridine; hydrogen fluoride; In acetonitrile; at 0 ℃; for 3h;

upstream raw materials:

(Z)-7-[(3R)-3-(tert-butyldimethylsilanyloxy)-5-oxo-cyclopent-1-enyl]hept-5-enoic acid isopropyl ester

Downstream raw materials:

lubiprostone

Refernces