Regioselective Monoesterification Study of the Diol in 1-C-(4,6-O-Benzylidene-β-D-glucopyranosyl) Acetone

It was found that all-protected and monoprotected products form simultaneously. However, the regioselectivity tends to favor the 3-substituted derivative.

Structural parameters have been determined by 1 H NMR, 13 C NMR, 1 H- 1 H correlation spectroscopy, and elemental analysis. Furthermore, a possible mechanism for the formation of intramolecular hydrogen-bond networks between the carbonyl group and 2-OH was described. The energy changes of the transition state in this reaction, as determined by a molecular modelling study, provided further evidence to assign the relative reactivities of each individual hydroxyl group.