330998-75-9Relevant academic research and scientific papers
Concise synthesis of 1-deoxy-4-O-β-D-galactopyranosyl-D-nojirimycin avoiding a glycosylation step
D'Andrea, Felicia,Catelani, Giorgio,Mariani, Manuela,Vecchi, Barbara
, p. 1139 - 1142 (2001)
2′,6′-Di-O-benzyl-2,3:5,6:3′,4′-tri-O-isopropylide nelactose dimethyl acetal was used as starting material for the preparation of the until now unknown 4-O-β-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-β-D-galactopyranosyl-D-nojirimycin derivatives in about 60% yield, through a double reductive amination reaction.
