85610-68-0

Basic information

• Product Name: (Z)-7-((1R,2R,3R)-3-((tert-butyldimethylsilyl)oxy)-2-((S,E)-3-((tert-butyldimethylsilyl)oxy)oct-1-en-1-yl)-5-oxocyclopentyl)hept-5-enoic acid
• Synonyms: (Z)-7-((1R,2R,3R)-3-((tert-butyldimethylsilyl)oxy)-2-((S,E)-3-((tert-butyldimethylsilyl)oxy)oct-1-en-1-yl)-5-oxocyclopentyl)hept-5-enoic acid
• CAS NO: 85610-68-0
• Molecular Weight: 580.996
• Mol File: 85610-68-0.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (Z)-7-((1R,2R,3R)-3-((tert-butyldimethylsilyl)oxy)-2-((S,E)-3-((tert-butyldimethylsilyl)oxy)oct-1-en-1-yl)-5-oxocyclopentyl)hept-5-enoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-7-((1R,2R,3R)-3-((tert-butyldimethylsilyl)oxy)-2-((S,E)-3-((tert-butyldimethylsilyl)oxy)oct-1-en-1-yl)-5-oxocyclopentyl)hept-5-enoic acid(85610-68-0)
• EPA Substance Registry System: (Z)-7-((1R,2R,3R)-3-((tert-butyldimethylsilyl)oxy)-2-((S,E)-3-((tert-butyldimethylsilyl)oxy)oct-1-en-1-yl)-5-oxocyclopentyl)hept-5-enoic acid(85610-68-0)

Safety Data

• Hazardous Substances Data: 85610-68-0(Hazardous Substances Data)

Upstream product

• 26054-46-6 (-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-one 

Downstream Products

• 13345-50-1 prostaglandin A₂ 
• 363-24-6 dinoprostone 

Relevant articles and documents

Access to a Key Building Block for the Prostaglandin Family via Stereocontrolled Organocatalytic Baeyer–Villiger Oxidation

A new protocol for the construction of a crucial bicyclic lactone of prostaglandins using a stereocontrolled organocatalytic Baeyer–Villiger (B-V) oxidation was developed. The key B-V oxidation of a racemic cyclobutanone derivative with aqueous hydrogen peroxide has enabled an early-stage construction of a bicyclic lactone skeleton in high enantiomeric excess (up to 95 %). The generated bicyclic lactone is fully primed with two desired stereocenters and enabled the synthesis of the entire family of prostaglandins according to Corey′s route. Furthermore, the reactivity and enantioselectivity of B-V oxidation of racemic bicyclic cyclobutanones were evaluated and 90–99 % ee was obtained, representing one of the most efficient routes to chiral lactones. This study further facilitates the synthesis of prostaglandins and chiral lactone-containing natural products to promote drug discovery.