Hydroxyl proton resonances of methyl 4,6-O-benzyIidene-α- and β-D-glucopyranosides and their derivatives in dimethyl sulfoxide solution

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Abstract
Proton magnetic resonance spectra of methyl 4,6-O-benzylidene-α- and β-D-glucopyranosides (1 and 10) and their mono-substituted derivatives are determined in dimethyl sulfoxide solution. Assignments of the hydroxyl group resonances of 1 and 10 are confirmed by means of INDOR techniques. It is shown that the position of the hydroxyl substituent of the mono-substituted derivatives of 1 and 10 can be determined by using the coupling constants JH—C—O—H. It is proposed that the vicinal diols of 1 and 10 give 1:1 associations with dimethyl sulfoxide molecules, and the C—H and O—H bonds at position 2 of the mono-substituted derivatives of 1 are approximately anti.

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