Concise synthesis of C-1-cyano-iminosugars via a new Staudinger/aza Wittig/Strecker multicomponent reaction strategy

被引：17
|
作者：
Zoidl, Manuel [1 ]
Mueller, Bernhard [1 ]
Torvisco, Ana [2 ]
Tysoe, Christina [4 ]
Benazza, Mohamed [3 ]
Siriwardena, Aloysius [3 ]
Withers, Stephen G. [4 ]
Wrodnigg, Tanja M. [1 ]
机构：
[1] Graz Univ Technol, Inst Organ Chem, Glycogrp, A-8010 Graz, Austria
[2] Graz Univ Technol, Inst Inorgan Chem, A-8010 Graz, Austria
[3] Univ Picardie Jules Verne, CNRS FRE 3517, Labe Glycochim Antimicrobiens & Agroressources, F-80039 Amiens, France
[4] Univ British Columbia, Dept Chem, Vancouver, BC V6T 1Z1, Canada
来源：
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2014年 / 24卷 / 12期
关键词：
Glycosidase inhibitor; Iminoalditol; Staudinger/aza Wittig Strecker; multicomponent reaction; Glucocerebrosidase; C-1-cyano-iminosugar building blocks; PHARMACOLOGICAL CHAPERONES; GLYCOSIDASE INHIBITORS; NATURAL OCCURRENCE; IMINOSUGARS; DISEASE; G(M1)-GANGLIOSIDOSIS; ALZHEIMERS;
D O I：
10.1016/j.bmcl.2014.03.069
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
A new Staudinger/aza Wittig/Strecker multicomponent reaction sequence to C-1-cyano iminoalditols has been developed. When applied to 5-azidodeoxy-D-xylose and -D-glucose as substrates the method leads smoothly in good yield and with excellent stereoselectivity to respectively, 1,5-dideoxy-1,5-imino-D-idurono nitrile and 2,6-didesoxy-2,6-imino-D-glycero-D-ido-heptononitrile. (C) 2014 Published by Elsevier Ltd.
引用
收藏
页码：2777 / 2780
页数：4
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