Stereoselective entry into the D-GalNAc series starting from the D-Gal one: a new access to N-acetyl-D-galactosamine and derivatives thereof

Guazzelli, Lorenzo and Catelani, Giorgio and D'Andrea, Felicia and Giannarelli, Alessia (2009) Stereoselective entry into the D-GalNAc series starting from the D-Gal one: a new access to N-acetyl-D-galactosamine and derivatives thereof. Carbohydrate Research, 344/20 (3). pp. 298-303. ISSN 0008-6215

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Abstract

A new stereoselective preparation of N-aceyl-D-galactosamine (1b) starting from the known p-methoxyphenyl 3,4-O-isopropylidene-6-O-(1-methoxy-1-methylethyl)-b-D-galactopyranoside (10) is described using a simple strategy based on (a) epimerization at C-2 of 10 via oxidation–reduction to give the talo derivative 11, (b) amination with configurational inversion at C-2 of 11 via a SN2-type reaction on its 2- imidazylate, (c) anomeric deprotection of the p-methoxyphenyl beta-D-galactosamine glycoside 14, (d) complete deprotection. Applying the same protocol to 2,3:5,6:30,40-tri-O-isopropylidene-60-O-(1-methoxy- 1-methylethyl)-lactose dimethyl acetal (4), directly obtained through acetonation of lactose, the disaccharide beta-D-GalNAcp-(1?4)-D-Glcp (1a) was obtained with complete stereoselectivity in good (40%) overall yield from lactose.

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