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Anomeric reactivity-based one-pot oligosaccharide synthesis: A rapid route to oligosaccharide libraries

Academic Article
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Overview

authors

  • Ye, X. S.
  • Wong, Chi-Huey

publication date

  • 2000

journal

  • Journal of Organic Chemistry  Journal

abstract

  • The assembly of an oligosaccharide library has been achieved in a practical and efficient manner employing a' one-pot sequential approach. With the help of the anomeric reactivity values of thioglycosides, using a thioglycoside (mono- or disaccharide) with one free hydroxyl group as acceptor and donor coupled with another fully protected thioglycoside, a di- or trisaccharide is selectively formed without self-condensation and subsequently reacted in situ with an anomerically inactive glycoside (mono- or disaccharide) to form a tri- or tetrasaccharide in high overall yield. The approach enables the rapid assembly of 33 linear or branched fully protected oligosaccharides using designed building blocks. These fully protected oligosaccharides have been partially or completely deprotected to create 29 more structures to further increase the diversity of the library.

subject areas

  • Carbohydrate Sequence
  • Catalysis
  • Hydroxyl Radical
  • Magnetic Resonance Spectroscopy
  • Molecular Sequence Data
  • Oligosaccharides
  • Thioglycosides
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Identity

International Standard Serial Number (ISSN)

  • 0022-3263

Digital Object Identifier (DOI)

  • 10.1021/jo991558w

PubMed ID

  • 10789453
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Additional Document Info

start page

  • 2410

end page

  • 2431

volume

  • 65

issue

  • 8

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