Issue 9, 2001
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

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

Vijaya Bhaskar K.,†a   Peter J. Duggan,a   David G. Humphrey,*b   Guy Y. Krippner,c   Victoria McCarla  and  Daniel A. Offermanna  

* Corresponding authors

a Centre for Green Chemistry, School of Chemistry, Monash University, PO Box 23, Clayton, Melbourne, Victoria, Australia
E-mail: peter.duggan@sci.monash.edu.au

b CSIRO Forestry and Forest Products, Private Bag 10, Clayton South, Melbourne, Victoria, Australia

c Biota Chemistry Laboratory, School of Chemistry, Monash University, PO Box 23, Clayton, Melbourne, Victoria, Australia

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.

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

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Article information

DOI
https://doi.org/10.1039/B009450L
Article type
Paper
Submitted
24 Nov 2000
Accepted
19 Feb 2001
First published
26 Mar 2001

J. Chem. Soc., Perkin Trans. 1, 2001, 1098-1102

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

V. Bhaskar K., P. J. Duggan, D. G. Humphrey, G. Y. Krippner, V. McCarl and D. A. Offermann, J. Chem. Soc., Perkin Trans. 1, 2001, 1098 DOI: 10.1039/B009450L

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