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Facile Aza‐Claisen Rearrangement of Glycals: Application in the Synthesis of 1‐Deoxy‐ L ‐iminosugars
Author(s) -
Gupta Preeti,
Vankar Yashwant D.
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200801301
Subject(s) - chemistry , claisen rearrangement , hydroxymethyl , stereochemistry , glycosyl
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 μ M ), 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)