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

页码：2777 / 2780

页数：4

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