1333933-41-7Relevant academic research and scientific papers
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
Lafont, Dominique,D'Attoma, Joseph,Gomez, Rejane,Goekjian, Peter G.
, p. 1197 - 1204 (2011)
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.
