Methyl 2-acetamido-2-deoxy-β-D-glucopyranoside (β-GlcNAcOCH(3)), (I), crystallizes from water as a dihydrate, C(9)H(17)NO(6)·H(2)O, containing two independent molecules [denoted (IA) and (IB)] in the asymmetric unit, whereas the crystal structure of methyl 2-formamido-2-deoxy-β-D-glucopyranoside (β-GlcNFmOCH(3)), (II), C(8)H(15)NO(6), also obtained from water, is devoid of solvent water molecul...

Monofunctionalization of trehalose, a widely-found symmetric plant disaccharide, was studied in a microreactor to give valuable kinetic insights that have allowed improvements in desymmetrization yields and the development of a reaction sequence for large scale monofunctionalizations that allow access to probes of trehalose's biological function.

Gualamycin is a water-soluble acaricide isolated from the culture broth of Streptomyces sp. NKl^S?1*. The structure was deduced to be 1 mainly from the spectral and/or X-ray crystallographic analyses of its disaccharide 2 and aglycone portions 32). The absolute structure of the disaccharide, however, remained undetermined. Herein, we confirm the absolute structure 1 by the enantiospeciflc synth...

A practical approach has been developed to convert glucals and rhamnals into disaccharides or glycoconjugates with high α-selectivity and yields (77-97%) using a trans-fused cyclic 3,4-O-disiloxane protecting group and TsOH⋅H2O (1 mol%) as a catalyst. Control of the anomeric selectivity arises from conformational locking of the intermediate oxacarbenium cation. Glucals outperform rhamnals becau...