Preparation, X-ray structure and reactivity of a stable glycosyl iodide
Literature Information
Jamie Bickley, Jennifer A. Cottrell, John R. Ferguson, Robert A. Field, John R. Harding, David L. Hughes, K. P. Ravindanathan Kartha, Jayne L. Law, Feodor Scheinmann, Andrew V. Stachulski
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.
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