Hydrolytic enzymes in the synthesis of carba-sugars:: application of the lipase from Pseudomonas fragi

被引：8

作者：

Tran, CH ^{[1
]}

Crout, DHG ^{[1
]}

机构：

[1] Univ Warwick, Dept Chem, Coventry CV4 7AL, W Midlands, England

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1998年 / 06期

关键词：

D O I：

10.1039/a708593a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Pig liver esterase-catalysed hydrolysis of (+/-)-endo-2-methoxycarbonyl-7-oxabicyclo[2.2.1]hept-5-ene 1a provides (-)-endo-7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylic acid 1b and (+)-endo-2-methoxycarbonyl-7-oxabicyclo[2.2.1]hept-5-ene 1a in 36 and 57% ee, respectively. Transesterification between (+/-)-2-exo-hydroxy-4,8-dioxatricyclo[4.2.1.0(3,7)]nonan-5-one 2a and vinyl acetate catalysed by the lipase from Pseudomonas fragi gives the acetate (-)-2b and alcohol (+)-2a in 91 and 94% ee, respectively, Optically pure acetate (-)-2b is obtained after removal of contaminating racemate from the impure acetate by crystallisation of(-)-2b of 91% ee (EtOH).

引用

页码：1065 / 1068

页数：4

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