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Novel efficient routes to heparin monosaccharides and disaccharides achieved via regio- and stereoselective glycosidation

Academic Article
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Overview

authors

  • Yu, H. N.
  • Furukawa, J.
  • Ikeda, T.
  • Wong, Chi-Huey

publication date

  • March 2004

journal

  • Organic Letters  Journal

abstract

  • A new methodology for the synthesis of heparin building blocks has been developed. We describe novel efficient routes to both L-iduronic acid and D-glucuronic acid acceptors. Glycosylation with thioglycosides donors gave corresponding disaccharides in a regio- and stereoselective fashion. An improved approach to synthesizing azido-glucose thioglycoside donor to render azido-sugar from mannose via nucleophilic substitution is described. [reaction: see text]

subject areas

  • Carbohydrate Sequence
  • Disaccharides
  • Glycosylation
  • Heparin
  • Molecular Sequence Data
  • Molecular Structure
  • Monosaccharides
  • Stereoisomerism
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Identity

International Standard Serial Number (ISSN)

  • 1523-7060

Digital Object Identifier (DOI)

  • 10.1021/ol036390m

PubMed ID

  • 14986959
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Additional Document Info

start page

  • 723

end page

  • 726

volume

  • 6

issue

  • 5

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