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Issue 11, 2003
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Preparation, X-ray structure and reactivity of a stable glycosyl iodide

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Abstract

Highly selective reaction of methyl tetra-O-pivaloyl-β-D-glucopyranuronate 2 with iodotrimethylsilane or (Me3Si)2 and I2 affords, in excellent yield, the ‘disarmed’ glycosyl iodide 1 which has good stability at 20 °C and excellent stability at 0 °C; the X-ray crystal structure of 1 is described, along with a comparison of its utility as a glycosyl donor to that of the corresponding bromide.

Graphical abstract: Preparation, X-ray structure and reactivity of a stable glycosyl iodide

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Publication details

The article was received on 07 Mar 2003, accepted on 02 Apr 2003 and first published on 01 May 2003


Article type: Communication
DOI: 10.1039/B302629A
Citation: Chem. Commun., 2003,0, 1266-1267

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    Preparation, X-ray structure and reactivity of a stable glycosyl iodide

    J. Bickley, J. A. Cottrell, J. R. Ferguson, R. A. Field, J. R. Harding, D. L. Hughes, K. P. Ravindanathan Kartha, J. L. Law, F. Scheinmann and A. V. Stachulski, Chem. Commun., 2003, 0, 1266
    DOI: 10.1039/B302629A

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