Abstract
The solvent dependences of the populations of the hydroxymethyl rotamers of methyl 2,3,4,6-tetra-O-[2H3]-α-d-glucopyranoside (2a) and methyl 2,3,4-tri-O-[2H3]-α-d-glucopyranoside (6) in 10 and 8 solvents, respectively, have been determined by analysis of 3JH5,H6R and 3JH5,H6S values and by consideration of evidence for hydrogen bonding through infrared spectroscopy and 3JH,OH values. The methods used to determine coupling constants in individual hydroxymethyl rotamers were reexamined, and an improved protocol was developed. When O-6 is methylated (2a), the populations of the hydroxymethyl rotamers are largely independent of solvent polarity at ratios of about 61:38:0 gg:gt:tg, except that a small population (<4%) of the tg rotamer appears in the most polar solvents at the expense of the gg rotamer. When O-6 is unsubstituted (6), there are substantial changes in rotamer population as solvent polarity increases due to loss of intramolecular hydrogen bonding and stabilization of the more polar rotamers. The ...
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