ENZYMATIC ACYLATION IN THE RESOLUTION OF METHYL THREO-2-HYDROXY-3-(4-METHOXYPHENYL)-3-(2-X-PHENYLTHIO)PROPIONATES IN ORGANIC-SOLVENTS

被引:63
作者
KANERVA, LT
SUNDHOLM, O
机构
[1] Department of Chemistry, University of Turku
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1993年 / 20期
关键词
D O I
10.1039/p19930002407
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A practical lipase PS (Pseudomonas cepacia)-catalysed resolution of methyl threo-2-hydroxy-3-(4-methoxyphenyl)-3-(2-X-phenylthio)propionates 3, the (2S,3S)-enantiomers of which are important intermediates in the diltiazem synthesis, has been performed using acetone oxime, and isopropenyl or vinyl acetates as acylating reagents in organic solvents. The substituent X in compounds 3 does not have a clear effect on the enzymatic enantioselectivity, but the time needed for the resolution depends on X. The immobilization of the enzyme on Celite or Chromosorb in the presence of sucrose greatly enhances enzymatic activity. The immobilized enzyme is stable for reuse.
引用
收藏
页码:2407 / 2410
页数:4
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