Rapid access to uronic acid-based mimetics of Kdn2en from D-glucurono-6,3-lactone

  • Carbohydr Res. 2000 Oct 6;328(4):445-8. doi: 10.1016/s0008-6215(00)00228-7.
P Florio  1 ,  R J Thomson ,  M von Itzstein
Affiliations
  • 1. Department of Medicinal Chemistry, Monash University, Parkville, Vic., Australia.
PMID: 11093699 DOI: 10.1016/s0008-6215(00)00228-7
Abstract

A concise route to novel mimetics of Kdn2en, based on delta4-uronic acids, from D-glucurono-6,3-lactone is presented. Uronic acid-based mimetics in which an aliphatic ether (O-glycoside), a thioether (S-glycoside), or acetamide takes the place of the natural C-6 glycerol sidechain of the sialic acid were synthesized from the key intermediate, methyl 2,3,4-tri-O-acetyl-alpha-D-glucopyranosyluronate bromide.

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