61628-05-5

Basic information

• Product Name: (3aR,4R,5R,6aS)-hexahydro-5-tert-butyldimethylsilyloxy-4-[(1E,3S)-3-tert-butyldimethylsilyloxy-(1E)-octenyl]-2H-cyclopenta[β]furan-2-one
• Synonyms: (3aR,4R,5R,6aS)-hexahydro-5-tert-butyldimethylsilyloxy-4-[(1E,3S)-3-tert-butyldimethylsilyloxy-(1E)-octenyl]-2H-cyclopenta[β]furan-2-one
• CAS NO: 61628-05-5
• Molecular Weight: 496.878
• Mol File: 61628-05-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (3aR,4R,5R,6aS)-hexahydro-5-tert-butyldimethylsilyloxy-4-[(1E,3S)-3-tert-butyldimethylsilyloxy-(1E)-octenyl]-2H-cyclopenta[β]furan-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (3aR,4R,5R,6aS)-hexahydro-5-tert-butyldimethylsilyloxy-4-[(1E,3S)-3-tert-butyldimethylsilyloxy-(1E)-octenyl]-2H-cyclopenta[β]furan-2-one(61628-05-5)
• EPA Substance Registry System: (3aR,4R,5R,6aS)-hexahydro-5-tert-butyldimethylsilyloxy-4-[(1E,3S)-3-tert-butyldimethylsilyloxy-(1E)-octenyl]-2H-cyclopenta[β]furan-2-one(61628-05-5)

Safety Data

• Hazardous Substances Data: 61628-05-5(Hazardous Substances Data)

Usage

General Description

The chemical compound "(3aR,4R,5R,6aS)-hexahydro-5-tert-butyldimethylsilyloxy-4-[(1E,3S)-3-tert-butyldimethylsilyloxy-(1E)-octenyl]-2H-cyclopenta[β]furan-2-one" is a complex molecule with a cyclopenta[b]furan core. It is a derivative of octenyl, with tert-butyldimethylsilyloxy groups attached to the carbon chain. Additionally, there are tert-butyldimethylsilyloxy groups attached to the cyclopenta[b]furan ring. The compound has a hexahydro structure, meaning that it has a six-membered carbon ring. (3aR,4R,5R,6aS)-hexahydro-5-tert-butyldimethylsilyloxy-4-[(1E,3S)-3-tert-butyldimethylsilyloxy-(1E)-octenyl]-2H-cyclopenta[β]furan-2-one has potential applications in organic synthesis and may be of interest to researchers in the fields of medicinal chemistry and chemical engineering.

Upstream product

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

Downstream Products

• 363-24-6 dinoprostone 
• 13345-50-1 prostaglandin A₂ 
• 64700-71-6 2,3-dinor-6-keto-prostaglandin F_1a 
• 98582-10-6 7-{(1R,2R,3R,5S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-oct-1-enyl]-cyclopentyl}-6-oxo-5-phenylsulfanyl-heptanoic acid methyl ester 
• 98582-06-0 1-{(1R,2R,3R,5S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-oct-1-enyl]-cyclopentyl}-3-phenylsulfanyl-propan-2-one 
• 63557-55-1 6-keto-PGF_1α methyl ester 

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.