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Glycosyl halides reduction

Hi) Reduction of Glycosyl Halides with Radical Rearrangement. The reduction of acetylated or benzoylated halides or selenides with a low concentration of tributylstannane leads to 2-deoxy sugar derivatives (Scheme 11). The driving force of this radical reaction is the 1,2-cA-selective migration of an ester group because of the stabilization of the radical at C-2.46... [Pg.151]

The favored formation of acetylated l-a-deuterio-l,5-anhydro-D-glucitol 78 in labeling experiments has been put forward to support the occurrence of carbohydrate radicals as intermediates in the photolytic decomposition of glucopyranosyl phenyl sulfone acetates104 as well as the Cp2TiBD4193 and zinc-silver/graphite-197 mediated reduction of glycosyl halides. Cationic intermediates would have favored the opposite stereochemistry 26... [Pg.106]

Scheme 32. Preparation of 1,5-anhydro-hexitols by reduction of glycosyl halides... Scheme 32. Preparation of 1,5-anhydro-hexitols by reduction of glycosyl halides...
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Glycosyl halide halides

Glycosyl halides

Halides reduction

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