Interplay of Protecting Groups and Side Chain Conformation in Glycopyranosides. Modulation of the Influence of Remote Substituents on Glycosylation?

ABSTRACT: The synthesis and conformational analysis of a series of phenyl 2,3,6-tri- O-benzyl-β-d-thio galacto- and glucopyranosides and their 6 S-deuterio isotopomers, with systematic variation of the protecting group at the 4-position, are described. For the galactopyranosides, replacement of a 4- O-benzyl ether by a 4- O-alkanoyl or aroyl ester results in a small but measurable shift in side chain population away from the trans, gauche conformation and in favor of the gauche, trans conformer. In the glucopyranoside series on the other hand, replacement of a 4- O-benzyl ether by a 4- O-alkanoyl or aroyl ester results in a small but measurable increase in the population of the trans, gauche conformer at the expense of the gauche, gauche conformer. The possible modulating effect of these conformatio

SUBMITTER: Dharuman S 

PROVIDER: S-EPMC6131524 | biostudies-literature | 2018 Sep

REPOSITORIES: biostudies-literature