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N-(phenylthio)-epsilon-caprolactam: A new promoter for the activation of thioglycosides

Academic Article
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Overview

authors

  • Duron, S. G.
  • Polat, T.
  • Wong, Chi-Huey

publication date

  • March 2004

journal

  • Organic Letters  Journal

abstract

  • N-(phenylthio)-epsilon-caprolactam (1) has been applied as a new promoter for the activation of thioglycosides. This proceeds by the reaction of 1 with trifluoromethansulfonic anhydride, which subsequently activates the thioglycoside for glycosidic bond formation. Notably, the reaction proceeds efficiently at room temperature and is adaptable to our reactivity-based one-pot oligosaccharide synthesis. [reaction: see text]

subject areas

  • Carbohydrate Sequence
  • Glycosylation
  • Lactams
  • Molecular Sequence Data
  • Stereoisomerism
  • Sulfides
  • Thioglycosides
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Identity

International Standard Serial Number (ISSN)

  • 1523-7060

Digital Object Identifier (DOI)

  • 10.1021/ol0400084

PubMed ID

  • 14986988
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Additional Document Info

start page

  • 839

end page

  • 841

volume

  • 6

issue

  • 5

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