Synthesis of regio- and stereospecifically C-deuterated derivatives of glycosidase inhibitors 1-deoxymannonojirimycin and 2,5-dideoxy-2,5-imino-D-mannitol by intramolecular reductive amination employing deuterium gas

被引：5

作者：

Fechter, MH ^{[1
]}

Gradnig, G ^{[1
]}

Berger, A ^{[1
]}

Mirtl, C ^{[1
]}

Schmid, W ^{[1
]}

Stütz, AE ^{[1
]}

机构：

[1] Graz Tech Univ, Inst Organ Chem, A-8010 Graz, Austria

来源：

CARBOHYDRATE RESEARCH | 1998年 / 309卷 / 04期

基金：

奥地利科学基金会;

关键词：

C-deuteration; deuterium gas; glycosidase inhibitor;

D O I：

10.1016/S0008-6215(98)00159-1

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

6-Azido-1,3,4-tri-O-benzyl-6-deoxy-D-fructofuranose can be easily obtained in two steps from the known 6,6'-diazido-6,6'-dideoxysucrose, which is available in two steps from sucrose. Cyclisation of this material by controlled hydrogenation with H-2(2) over Raney nickel and concomitant intramolecular reductive amination gave 3,4,6-tri-O-benzyl-1,5-dideoxy-1,5-imino-D-(5-H-2)mannitol, a partially protected derivative of 1-deoxymannonojirimycin. Conventional deprotection furnished 1-deoxy-(5-H-2)mannonojirimycin. Reduction and intramolecular reductive amination of free 5-azido-5-deoxy-D-fructopyranose gave 2,5-dideoxy-2,5-imino-D-(5-H-2)mannitol in one step. Likewise, 2,5-dideoxy-2,5-imino-D-(5-2H)glucitol was obtained from 5-azido-5-deoxy-L-sorbopyranose. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：367 / 374

页数：8

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