Inositols: The Effect of Bulky Substituents on Conformations

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Contents Vol 60(8)

doi:10.1071/CH07092

Inositols: The Effect of Bulky Substituents on Conformations*

Stephen J. Angyal ^A ^C, J. Edgar Anderson ^B, Donald C. Craig ^A

^A School of Chemistry, University of New South Wales, Sydney NSW 2052, Australia.
^B Chemistry Department, University College, Gower Street, London WC1E 6BT, UK.
^C Corresponding author. Email: s.angyal@unsw.edu.au





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Australian Journal of Chemistry 60(8) 572–577 http://dx.doi.org/10.1071/CH07092
Submitted: 5 March 2007 Accepted: 27 May 2007 Published online: 9 August 2007

Abstract

Inositols have been converted into their triphenylsilyl derivatives. In all cases only five substituents could be introduced, the remaining free hydroxy group being hindered. The derivative of myo-inositol and one of two of neo-inositol were found to be in the inverted chair conformation, but those of other inositols are in the normal chair form. The structures of two penta-substituted derivatives have been determined by X-ray crystallography.

^* This paper is Part 44 (and the last) of the series Cyclitols. For Part 43, see S. J. Angyal, Carbohydr. Res. 2000, 325, 313. Part 1 is S. J. Angyal, C. G. Macdonald, J. Chem. Soc., 1952, 686.