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Synlett 1996; 1996(2): 159-162
DOI: 10.1055/s-1996-5349
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Polymer-supported solution synthesis of oligosaccharides: Probing glycosylations of MPEG-DOX-OH with 2-acetamidoglycopyranosyl derivatives

György Hodosi, Jiri J. Krepinsky*
  • *Department of Molecular and Medical Genetics and Protein Engineering Network Centres of Excellence, University of Toronto, Toronto, Ontario M5S 1A8, Canada
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Publication Date:
31 December 2000 (online)

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The title glycosylations were optimized on the basis of better understanding of the mechanism of glycosylation with GlcNAc-derived glycosylating agents. The origin of acyl transfer to accepting hydroxyls from some glycosylating agents was identified. It is shown that oxazolines are not intermediates in these glycosylations and therefore cannot explain the trans stereospecifity of these reactions.

SN2 substitution - oxazolinium ion - beta selectivity - polymer supported - glycosylation