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Chemoselective glycosidation strategy based on glycosyl donors and acceptors carrying phosphorus-containing leaving groups: a convergent synthesis of ganglioside GM3

โœ Scribed by Hiroki Sakamoto; Seiichi Nakamura; Toshifumi Tsuda; Shunichi Hashimoto

Book ID
104210894
Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
117 KB
Volume
41
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

A convergent synthesis of ganglioside GM 3 has been achieved by capitalizing on three different phosphorus-containing leaving groups, in which the key features involve a chemo-and regioselective a-glycosidation of sialyl phosphite with partially benzylated galactosyl tetramethylphosphorodiamidate by the aid of trifluoromethanesulfonic acid and a traditionally uncommon coupling of an a-sialyl-( 23)galactosyl donor with a glucosylceramide building block which has the b-O-linked ceramide prebuilt into the glucose by a diphenyl phosphate method.

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