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2-deoxy-2-iodo- and 2-deoxy-2-bromo-alpha-glucopyranosyl trichloroacetimidates: highly reactive and stereoselective donors for the synthesis of 2-deoxy-beta-glycosides

Academic Article
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Overview

authors

  • Roush, William
  • Gung, B. W.
  • Bennett, C. E.

publication date

  • September 1999

journal

  • Organic Letters  Journal

abstract

  • [formula: see text] 2-Deoxy-2-iodo- and 2-deoxy-2-bromoglucopyranosyl trichloroacetimidates 8-10 and 22 are extremely useful precursors of 2-deoxy-beta-glycosides. These reactive glycosyl donors undergo highly stereoselective glycosidation reactions at -78 degrees C with a range of glycosyl acceptors using TBS-OTf as the activating agent. beta-Glycosides are obtained with > or = 19:1 selectivity in six of the seven examples reported herein.

subject areas

  • Acetamides
  • Carbohydrate Sequence
  • Chloroacetates
  • Glycosides
  • Molecular Sequence Data
  • Trichloroacetic Acid
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Identity

International Standard Serial Number (ISSN)

  • 1523-7060

Digital Object Identifier (DOI)

  • 10.1021/ol9908070

PubMed ID

  • 10823218
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Additional Document Info

start page

  • 891

end page

  • 893

volume

  • 1

issue

  • 6

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