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Synthesis of Cluster N-Glycosides Based on a β-Cyclodextrin Core

✍ Scribed by Juan J. García-López; Francisco Santoyo-González; Antonio Vargas-Berenguel; Juan J. Giménez-Martínez

Publisher
John Wiley and Sons
Year
1999
Tongue
English
Weight
281 KB
Volume
5
Category
Article
ISSN
0947-6539

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✦ Synopsis

A convenient method for the synthesis of b-d-gluco-, b-d-galacto-, 2-acetamido-2-deoxy-b-d-gluco-and ad-mannopyranosylamine clusters based on cyclomaltoheptaose (b-cyclodextrin) is presented. The synthesis involves: 1) the one-pot synthesis of the acetylated chloroacetyl N-glycoside derivatives of d-glucose, d-galactose, 2-acetamido-2-deoxy-d-glucose and d-mannose from the corresponding glycosyl azides, 2) conversion of the chloroacetyl N-glycosides into their isothiouronium derivatives, then 3) attachment of the Nglycosides onto heptakis(6-deoxy-6-iodo) and heptakis(6-chloroacetamido-6deoxy) b-cyclodextrin by means of nu-cleophilic displacement with caesium carbonate in dimethylformamide, and 4) de-O-acetylation of b-cyclodextrin derivatives. The chloroacetyl N-glycoside derivatives were easily prepared by mild reduction of the azide function by one of two methods: a) by the Staudinger reaction, with nBu 3 P, and b) with 1,3propanedithiol, as reducing reagents.

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