Carbohydrate Research p. 173 - 194 (1996)
Update date:2022-08-03
Topics:
Ogawa, Yuji
Lei, Ping-Sheng
Kovac, Pavol
The title substances were prepared from intermediate, fully acetylated α-trimethylsilylethyl (SE) glycosides. The latter were assembled in a blockwise manner, using as the glycosyl donor the α-glycosyl chloride of a disaccharide bearing two 4-azido-4-deoxy functions. Next, the azido groups in the assembled hexasaccharides were converted to the corresponding amines, and these were acylated with 4-O-benzyl-3-deoxy-L-glycero-tetronic acid in the presence of a water-soluble carbodiimide. The SE glycosides were then transformed to glycosyl imidates, and these were coupled with methyl 6-hythoxyhexanoate or methyl 2-(2-hydroxyethylthio)propionate. The aglycons in the glycosides thus obtained were then converted to the corresponding carboxylic acids or acyl hydrazides. Such compounds are suitable for linking to proteins to obtain neoglycoproteins.
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