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Boronic Acids as Phase-Transfer Reagents for Fischer Glycosidations in Low-Polarity Solvents
journal contribution
posted on 2017-10-13, 20:48 authored by Sanjay Manhas, Mark S. TaylorProtocols 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.
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pyranoside productsPhase-Transfer Reagentsphase-transfer reagentboronic estersfuranosideboronic aciddiol groupsFischer GlycosidationsLow-Polarity Solvents Protocolsphenylboronic acidsubstrate-derived boronic esterrate accelerationglycoside-derived boronic estersBoronic AcidsFischer glycosidationsComputational modelingpyranoside-selective pathwayfunctionalized glycosides
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