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Boronic Acids as Phase-Transfer Reagents for Fischer Glycosidations in Low-Polarity Solvents

By Sanjay Manhas (4512943) and Mark S. Taylor (611990)


Protocols employing phenylboronic acid as a phase-transfer reagent for Fischer glycosidations in low-polarity organic solvents are described. In addition to providing rate acceleration, the formation of a substrate-derived boronic ester alters the course of the reaction by selective promotion of a furanoside- or pyranoside-selective pathway. Computational modeling of the relative energies of the glycoside-derived boronic esters provides results that are qualitatively consistent with the observed distributions of furanoside versus pyranoside products. The boronic esters that are obtained as direct products of these reactions serve as protected intermediates for the synthesis of functionalized glycosides. Complexation of particular diol groups by the boronic acid also enables selective transformations of mixtures of carbohydrates

Topics: Biochemistry, Genetics, Pharmacology, Evolutionary Biology, Infectious Diseases, Plant Biology, Astronomical and Space Sciences not elsewhere classified, Chemical Sciences not elsewhere classified, Information Systems not elsewhere classified, pyranoside products, Phase-Transfer Reagents, phase-transfer reagent, boronic esters, furanoside, boronic acid, diol groups, Fischer Glycosidations, Low-Polarity Solvents Protocols, phenylboronic acid, substrate-derived boronic ester, rate acceleration, glycoside-derived boronic esters, Boronic Acids, Fischer glycosidations, Computational modeling, pyranoside-selective pathway, functionalized glycosides
Year: 2017
DOI identifier: 10.1021/acs.joc.7b01880.s001
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Provided by: FigShare
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