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A concise synthesis of glycosyl-α-amino acid derivatives via homologation of dialdoses into bromo uronic acids and esters

✍ Scribed by Claude Grison; Stéphane Dumarçay; Philippe Coutrot

Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
131 KB
Volume
44
Category
Article
ISSN
0040-4039

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✦ Synopsis

The synthesis of the compounds of the title involves three steps from dialdoses. The reaction between potassium dibromoacetonitrile carbanion and protected dialdoses provides corresponding b-bromo-a-ketonitriles that are easily transformed into a-bromo esters by treatment with methanol or isopropanol or a-bromo acids by treatment with t-BuOH. Substitution of the bromine by sodium azide onto these last compounds and subsequent catalytic hydrogenation of the azide group afford the targeted glycosyl-a-amino acid derivatives. This methodology represents the most rapid access to the key a-amino acid moiety of polyoxins.

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