Facile Aza‐Claisen Rearrangement of Glycals: Application in the Synthesis of 1‐Deoxy‐ L ‐iminosugars | Zendy

Gupta Preeti | Zendy; Vankar Yashwant D. | Zendy

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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)

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