57930-46-8

Basic information

• Product Name: (3aR,4S,5R,6aS)-4-[(Acetyloxy)methyl]hexahydro-5-hydroxy-2H-cyclopenta[b]furan-2-one
• Synonyms: (3aR,4S,5R,6aS)-4-[(Acetyloxy)methyl]hexahydro-5-hydroxy-2H-cyclopenta[b]furan-2-one;[(3aR,4S,5R,6aS)-5-Hydroxy-2-oxohexahydro-2H-cyclopenta[b]furan-4 -yl]methyl acetate
• CAS NO: 57930-46-8
• Molecular Formula: C₁₀H₁₄O₅
• Molecular Weight: 214.21516
• Mol File: 57930-46-8.mol

Chemical Properties

• Boiling Point: 383℃
• Flash Point: 153℃
• Appearance: /
• Density: 1.297
• CAS DataBase Reference: (3aR,4S,5R,6aS)-4-[(Acetyloxy)methyl]hexahydro-5-hydroxy-2H-cyclopenta[b]furan-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (3aR,4S,5R,6aS)-4-[(Acetyloxy)methyl]hexahydro-5-hydroxy-2H-cyclopenta[b]furan-2-one(57930-46-8)
• EPA Substance Registry System: (3aR,4S,5R,6aS)-4-[(Acetyloxy)methyl]hexahydro-5-hydroxy-2H-cyclopenta[b]furan-2-one(57930-46-8)

Safety Data

• Hazardous Substances Data: 57930-46-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(3aR,4S,5R,6aS)-4-[(Acetyloxy)methyl]hexahydro-5-hydroxy-2H-cyclopenta[b]furan-2-one is used as a potential pharmaceutical agent for its unique structure and functional groups. (3aR,4S,5R,6aS)-4-[(Acetyloxy)methyl]hexahydro-5-hydroxy-2H-cyclopenta[b]furan-2-one's ester and alcohol functionalities may contribute to its interaction with biological targets, offering a range of therapeutic applications.
Used in Biological Research:
In the field of biological research, (3aR,4S,5R,6aS)-4-[(Acetyloxy)methyl]hexahydro-5-hydroxy-2H-cyclopenta[b]furan-2-one serves as a valuable compound for studying the effects of its unique structure and functional groups on biological systems. It may be utilized in assays and experiments to explore its potential as a bioactive molecule with applications in drug discovery and development.

Upstream product

• 50-00-0 formaldehyd 
• 26054-46-6 (-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-one 
• 108-05-4 vinyl acetate 
• 54423-47-1 (+/-)-(3aα,4α,5β,6aα)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopentafuran-2-one 
• 90529-18-3 (1SR, 5RS, 6RS, 7RS)-7-acetoxy-6-acetoxymethyl-2-oxabicyclo<3.3.0>octan-3-one 
• 64-19-7 acetic acid 

Downstream Products

• 32233-40-2 (3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one 
• 39968-95-1 (3aR,4S,5R,6aS)-5-[(tert-butyldimethylsilyl)oxy]-4-(hydroxymethyl)-hexahydro-2H-cyclopenta[b]furan-2-one 

Relevant articles and documents

Prins Reaction of 2-Oxabicyclooct-6-en-3-one and Related Derivatives

Reaction of formaldehyde with the title olefinic lactone in acetic acid affords diacetate of 1,3-diol (2a) as the main product in 50-60percent yield via regioselective trans-addition.Less favourable results were obtained with related bicyclic derivatives.

Enzymes in Organic Synthesis, 8: Synthesis of Enantiomerically Pure Prostaglandin Intermediates by Enzymatic Transesterification of (1S*,5R*,6R*,7R*)-(+/-)-7-Hydroxy-6-hydroxymethyl-2-oxabicyclooctan-3-one

Lipase Amano PS is a suitable biocatalyst for the highly regio- and enantioselective transesterification of the racemic prostaglandin building block (1S*,5R*,6R*,7R*)-(+/-)-7-hydroxy-6-hydroxymethyl-2-oxabicyclooctan-3-one (rac-1) yielding (1S,5R,6R,7R)-(-)-6-acetoxymethyl-7-hydroxy-2-oxabicyclooctan-3-one (2) and the unreacted (1R,5S,6S,7S)-(+)-enantiomer ent-1.Key Words: Prostaglandin intermediates / Enzymatic transformations / Lipases in organic solvents

Efficient enzymatic preparation of (+)- and (-)Corey lactone derivatives

Two pairs of Corey lactone derivatives, (+)-1, (-)-2 and (+)-3, (-)-4 have been efficiently prepared in high optical purity by enzymatic esterification and enzymatic hydrolysis catalyzed by lipases from Pseudomonas sp.

Enzymes in Organic Synthesis. 2. Synthesis of Enantiomerically Pure Prostaglandin Intermediates by Enzymatic Hydrolysis of (1SR, 5RS, 6RS, 7RS)-7-Acetoxy-6-acetoxymethyl-2-oxabicyclooctan-3-one

Subtilisin DY as well as alkaline protease from Bacillus licheniformis 41 p catalyze the hydrolysis of (1SR, 5RS, 6RS, 7RS)-7-acetoxy-6-acetoxymethyl-2-oxabicyclooctan-3-one (rac-1) with practically useful enantio- and regioselectivity.Under the hitherto found optimal conditions (1S, 5R, 6R, 7R)-7-hydroxy-6-hydroxymethyl-2-oxabicyclooctan-3-one (4), an important intermediate in prostaglandine syntheses, could be prepared in a yield of 16percent with an enantiomeric excess of 99percent.The enantiomer (ent-4) was obtained with the same enantiomeric excess in 20percent yield.The chemical yields are related to the racemic starting material rac-1.