2',6'-Di-O-benzyl-2,3:5,6:3',4'-tri-O-isopropylidenelactose dimethyl acetal was used as starting material for the preparation of the until now unknown 4-O-beta-D-galactopyranosyl-D-xylo-hexos-5-ulose derivatives 7–9, through selective C-5 oxidation of its partially deprotected derivatives 4–6. Hydrolysis of 7–9 with aq. CF3COOH led to deprotected 1,5-dicarbonyl disaccharides 11–12, diastereoselectively transformed without purification into 1-deoxy-4-O-beta-D-galactopyranosyl-D-nojirimycin derivatives in about 60% yield, through a double reductive amination reaction
Concise Synthesis of 1-deoxy-4-O-beta-D-galactopyranosyl-D-nojirimycin avoiding a glycosylation step
D'ANDREA, FELICIA;CATELANI, GIORGIO;
2001-01-01
Abstract
2',6'-Di-O-benzyl-2,3:5,6:3',4'-tri-O-isopropylidenelactose dimethyl acetal was used as starting material for the preparation of the until now unknown 4-O-beta-D-galactopyranosyl-D-xylo-hexos-5-ulose derivatives 7–9, through selective C-5 oxidation of its partially deprotected derivatives 4–6. Hydrolysis of 7–9 with aq. CF3COOH led to deprotected 1,5-dicarbonyl disaccharides 11–12, diastereoselectively transformed without purification into 1-deoxy-4-O-beta-D-galactopyranosyl-D-nojirimycin derivatives in about 60% yield, through a double reductive amination reactionFile in questo prodotto:
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