New synthesis of 1,4-dideoxy-1,4-imino-D-galactitol from D-glucose propane-1,3-diyl dithioacetal

被引：9
|
作者：
Pham-Huu, DP
Gizaw, Y
BeMiller, JN
Petrus, L
机构：
[1] Purdue Univ, Whistler Ctr Carbohydrate Res, W Lafayette, IN 47907 USA
[2] Procter & Gamble Co, Miami Valley Labs, Cincinnati, OH 45253 USA
[3] Slovak Acad Sci, Inst Chem, Bratislava 84238, Slovakia
来源：
TETRAHEDRON LETTERS | 2002年 / 43卷 / 03期
关键词：
dithioacetals; amino sugars; azasugars; pyrrolidines; Pd-catalyzed hydrogenations;
D O I：
10.1016/S0040-4039(01)02167-0
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The treatment of 4-azido-4-deoxy-2,3:5,6-di-O-isopropylidene-D-galactose propane-1,3-diyl dithioacetal (derived from D-glucose) with mercuric chloride and mercuric oxide in aqueous acetone afforded 4-azido-4-deoxy-2,3:5,6-di-O-isopropylidene-D-galactose. Acid-catalyzed deprotection of the azido derivative, followed by catalytic hydrogenation and concomitant intramolecular reductive amination in the presence of 10% palladium on carbon, gave 1,4-dideoxy-1,4-imino-D-galactitol in good yield. (C) 2002 Published by Elsevier Science Ltd.
引用
收藏
页码：383 / 385
页数：3
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