PRODUCTION OF OPTICALLY ACTIVE 4-PENTEN-2-OL DERIVATIVE

摘要

PURPOSE:To industrially obtain an optically active 4-penten-1-ol derivative useful for medicines and agricultural chemicals at a low cost, by optically resolving a specific ester with a microorganism-derived enzyme having stereoselective esterase activity. CONSTITUTION:An enzyme (e.g. lipase), derived from Chromobacterium viscosum and having stereoselective esterase activity is added to a reaction solution prepared by suspending 2-60wt./vol.% ester expressed by formula I (R is 1-7C aliphatic hydrocarbon group) so as to provide 1:1-1,000 weight ratio of the enzyme to the above-mentioned ester. The resultant reaction solution is then subjected to asymmetric hydrolytic reaction at 10-45 deg.C while adjusting the pH to 6-7.5 with NaOH to carry out optical resolution and form an optically active alcohol (4-penten-1-ol) expressed by formula II (* indicates asymmetric carbon) and an optically active ester expressed by formula III in the reaction solution. The resultant product is then extracted with methylene chloride, concentrated and subjected to separation treatment by silica gel column chromatographic operation to collect the aimed optically active 4-penten-2-ol derivative.