Lipase mediated desymmetrization of meso 2,6-di(acetoxymethyl)tetrahydropyran-4-one derivatives. An innovative route to enantiopure 2,4,6-trifunctionalized C-glycosides

被引:26
作者
Lampe, TFJ
Hoffmann, HMR
Bornscheuer, UT
机构
[1] UNIV HANNOVER,DEPT ORGAN CHEM,D-30167 HANNOVER,GERMANY
[2] UNIV STUTTGART,INST TECH BIOCHEM,D-70569 STUTTGART,GERMANY
关键词
D O I
10.1016/0957-4166(96)00380-1
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The desymmetrization of several meso-configurated 2,4,6-trifunctionalized tetrahydropyrans was studied. Amongst the derivatives investigated the conformationally more rigid spiro ketal 8b afforded hydroxy-acetate (-)-12 in excellent chemical yield and enantiomeric excess. The absolute configuration of the resulting 2,4,6-trifunctionalized C-glycosides was established by X-ray crystal diffraction. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码:2889 / 2900
页数:12
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