125226-81-5Relevant articles and documents
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
Theil, Fritz,Schick, Hans,Nedkov, Peter,Boehme, Monika,Haefner, Barbara,Schwarz, Sigfrid
, p. 893 - 899 (2007/10/02)
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.
