Phenylboronic acid as a labile protective agent: the selective derivatisation of 1,2,3-triols

doi:10.1039/B009450L

Paper

Phenylboronic acid as a labile protective agent: the selective derivatisation of 1,2,3-triols

Published 2001 · V. Bhaskar K, Peter J. Duggan, David G. Humphrey

Journal of The Chemical Society-perkin Transactions 1

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10

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Abstract

The ability of phenylboronic acid to act as a labile protective agent for open-chain 1,2,3-triols is demonstrated in the highly selective terminal derivatisation of D-mannitol and an antiviral sialic acid derivative. Protection, derivatisation and deprotection are carried out in a single pot, yielding analytically pure products in moderate yield, without the need for chromatography or formal recrystallisation steps. In both classes of compound, the selectivity of protection is found to be complementary to existing methods, providing access to relatively uncommon 1,6-diesters and the 1,6-bis(benzyl ether) of D-mannitol, and 9-o-acylsialic acid derivatives.

Study Snapshot

Phenylboronic acid acts as a labile protective agent for 1,2,3-triols, enabling selective derivatisation of D-mannitol and an antiviral sialic acid derivative in a single pot, without chromatography or formal recrystallization steps.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Phenylboronic acid as a labile protective agent: the selective derivatisation of 1,2,3-triols

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