Epoxidation of glycals with oxone–acetone–tetrabutylammonium hydrogen sulfate: a convenient access to simple β-d-glycosides and to α-d-mannosamine and d-talosamine donors

Add time:08/14/2019    Source:sciencedirect.com

The addition of a phase transfer catalyst during the epoxidation of perbenzylated glycals with oxone–acetone under biphasic conditions allows their complete epoxidation. The epoxides were readily transformed into methyl 1,2-trans-β-d-glycosides or 1,2-trans-β-d-glycopyranosyl azides (d-gluco and-d-galacto configurations) bearing a free hydroxyl group at the 2-position. These glycosyl azides were converted to alkyl 1,2-trans-2-acetamido-2-deoxy-α-d-pyranosides or alkyl 2-allyloxycarbonylamino-2-deoxy-α-d-pyranosides (d-manno and d-talo configurations) by a Staudinger reaction and a double inversion of configuration at C-1 and C-2.

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