A SIMPLE CONVERGENT SYNTHESIS OF THE MANNOSIDASE INHIBITOR 1-DEOXYMANNONOJIRIMYCIN FROM SUCROSE

被引：45

作者：

DERAADT, A ^{[1
]}

STUTZ, AE ^{[1
]}

机构：

[1] GRAZ TECH UNIV,INST ORGAN CHEM,STREMAYRGASSE 16,A-8010 GRAZ,AUSTRIA

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 02期

关键词：

1-DEOXYMANNONOJIRIMYCIN; MANNOSIDASE INHIBITOR; GLUCOSE ISOMERASE; SUCROSE; SYNTHESIS;

D O I：

10.1016/0040-4039(92)88046-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The glycosidase inhibitor 1-deoxymannonojirimycin (1,5-dideoxy-1,5-imino-D-mannitol) was synthesized in four simple steps from sucrose via 6,6'-diazido-6,6'-dideoxysucrose and 6-azido-6-deoxy-D-fructofuranose. The ''isomeric ballast'' of the sequence, 6-azido-6-deoxy-D-glucose, could be partially converted into 6-azido-6-deoxy-D-fructofuranose with the aid of glucose isomerase (E.C. 5.3.1.5) demonstrating a novel synthetic application of this enzyme. The sequence allows access to multigramm quantities of 1-deoxymannonojirimycin in over 30 % overall yield without the need for expensive reagents and protecting group manipulations.

引用

页码：189 / 192

页数：4

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