Chemical and enzymatic diastereoselective cleavage of beta-D-galactopyranosylsulfoxides

被引：30

作者：

Khiar, N

Alonso, I

Rodriguez, N

FernandezMayoralas, A

JimenezBarbero, J

Nieto, O

Cano, F

FocesFoces, C

MartinLomas, M

机构：

[1] CSIC,INST INVEST QUIM,SEVILLE 41092,SPAIN

[2] CSIC,GRP CARBOHIDRATOS,INST QUIM ORGAN,E-28006 MADRID,SPAIN

[3] CSIC,INST QUIM FIS ROCASOLANO,DEPT CRISTALOG,E-28806 MADRID,SPAIN

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 47期

关键词：

D O I：

10.1016/S0040-4039(97)10164-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The self induced diastereoselective oxidation of several thio-beta D-galactopyranosides to the corresponding sulfoxides, has been shown to occur in high yield. Up to 74% diastereomeric excess could be obtained depending on the structure and the conformation of the starting thioglycoside.Rs and Ss Phenylsulfinyl-beta-D-galactopyranosides have been obtained in optically pure forms, their chemical as well as enzymatic hydrolysis with triflic acid and with beta-galactosidase have been shown to proceed diastereoselectively, the structure of the sulfoxide 4'S with the S configuration at the sulfinyl sulfur has been determined by X-ray analysis. (C) 1997 Elsevier Science Ltd.

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页码：8267 / 8270

页数：4

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