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

Highly selective reaction of methyl tetra-O-pivaloyl-beta-D-glucopyranuronate 2 with iodotrimethylsilane or (Me3Si)(2) and I-2 affords, in excellent yield, the 'disarmed' glycosyl iodide 1 which has good stability at 20 degreesC and excellent stability at 0 degreesC; 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.