125226-80-4

Upstream product

• 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 

Relevant academic research and scientific papers

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

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.