A general method for the synthesis of C-glycosides of nojirimycin

被引：0
作者：
Fuchss, T [1 ]
Streicher, H [1 ]
Schmidt, RR [1 ]
机构：
[1] UNIV KONSTANZ,FAK CHEM,D-78434 CONSTANCE,GERMANY
来源：
LIEBIGS ANNALEN-RECUEIL | 1997年 / 07期
关键词：
C-glycosides; azasugars; piperidinosyl fluoride; O-piperidinosyl trichloroacetimidate; nojirimycin; deoxynojirimycin; glycosylations;
D O I：
暂无
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Methyl 2,3,4,6-tetra-O-acetyl-N-(benzyloxycarbonyl)nojirimycin (3) can be readily transformed into the corresponding azaglycal 6 or fluoride 7, which are versatile glycosyl/piperidinosyl donors. Reaction of 7 with allyltrimethylsilane, propinyltrimethylsilane, trimethylsilyl cyanide, and trimethylsilyl enol ether as carbon nucleophiles, afforded, in the presence of BF3 . OEt2 as catalyst, the corresponding C-glycosides 8-10 and 12-14 in good yields. The anomeric configurations of the C-glycosides are ascertained with the help of ROESY-NMR data.
引用
收藏
页码：1315 / 1321
页数：7
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