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Facile Aza-Claisen Rearrangement of Glycals: Application in the Synthesis of 1-Deoxy-L-iminosugars

✍ Scribed by Preeti Gupta; Yashwant D. Vankar

Publisher: John Wiley and Sons
Year: 2009
Tongue: English
Weight: 261 KB
Volume: 2009
Category: Article
ISSN: 1434-193X
DOI: 10.1002/ejoc.200801301

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✦ Synopsis

Abstract

2‐C‐Methylene‐N‐glycosyl amides have been obtained from 2‐(hydroxymethyl)glycals through a facile aza‐Claisen rearrangement. This rearrangement has also been utilized in the synthesis of L‐allo‐deoxynojirimycin, a moderate inhibitor of human lysosomal α‐mannosidase (IC~50~ = 64 μM), and two new C‐5‐(hydroxymethyl) analogues of L‐altro‐deoxynojirimycin and L‐ido‐deoxynojirimycin.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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