Synthesis of β-Mannopyranosides from α-Epimers by Radical Inversion. 1,6-Hydrogen Transfer Reactions of 2-O-(2-Bromoaryl)dimethylsilyl-α-methyl-D-mannopyranosides

Article abstract of DOI:10.1016/S0040-4039(00)73451-4

Intramolecular hydrogen transfer reactions of 3-O-acyl-α-methyl-D-mannopyranosides occur in a 1,6-fashion to give inverted β-mannopyranosides.The yields are limited by competing 1,5-hydrogen transfer reactions that give isomeric α-glucopyranosides.