26054-65-9

Usage

Uses

Used in Pharmaceutical Industry:
(1S,5R,6R,7R)-(-)-2-oxa-6-(hydroxymethyl)-7-acetoxybicyclo<3.3.0>-octan-3-one is used as a potential pharmaceutical compound for its unique structure and functional groups. The specific stereochemistry and presence of various functional groups may allow it to interact with biological targets or be modified for specific therapeutic purposes.
Used in Chemical Industry:
In the chemical industry, (1S,5R,6R,7R)-(-)-2-oxa-6-(hydroxymethyl)-7-acetoxybicyclo<3.3.0>-octan-3-one may be utilized as a building block or intermediate in the synthesis of more complex molecules. Its unique structure and functional groups could be exploited to create novel chemical entities with specific properties or reactivity.

Upstream product

• 50-00-0 formaldehyd 
• 26054-46-6 (-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-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 
• 84786-90-3 Acetic acid (3aR,4S,5R,6aS)-4-(tert-butyl-diphenyl-silanyloxymethyl)-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester 
• 84786-84-5 Benzoic acid (7S,8R,9S)-9-(tert-butyl-diphenyl-silanyloxymethyl)-8-[(Z)-4-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-but-2-enyl]-1,4-dithia-spiro[4.4]non-7-yl ester 
• 84786-85-6 C₄₁H₅₀O₆S₂Si 
• 84786-87-8 C₃₁H₃₈O₈S₂ 
• 84786-93-6 C₃₁H₄₀O₈S₃ 
• 84786-88-9 C₃₁H₄₀O₈S₂ 
• 84786-83-4 (7S,8R,9S)-9-(tert-Butyl-diphenyl-silanyloxymethyl)-8-[(Z)-4-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-but-2-enyl]-1,4-dithia-spiro[4.4]nonan-7-ol 
• 84786-92-5 C₂₅H₃₀O₆S₂ 
• 84786-86-7 C₂₅H₃₂O₆S₂ 
• 84786-81-2 C₂₆H₃₂O₃S₂Si 
• 84800-84-0 C₂₆H₃₄O₃S₂Si 
• 84786-91-4 (3aR,4S,6aS)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-tetrahydro-cyclopenta[b]furan-2,5-dione 
• 70803-92-8 6-[(1R,2R,3S)-2-((Z)-4-Carboxy-but-2-enyl)-3-hydroxy-5-oxo-cyclopentyl]-4-oxo-hexanoic acid 

Relevant academic research and scientific papers

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. 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.