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Rapid access to uronic acid-based mimetics of Kdn2en from D-glucurono-6,3-lactone
P Florio1, R J Thomson, M von Itzstein
1Department of Medicinal Chemistry, Monash University, Parkville, Vic., Australia.
Carbohydrate Research
|November 28, 2000
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.