Tin-mediated regioselective acylation of unprotected sugars on solid phase

Methyl α-D-glucopyranoside, methyl α-D-mannopyranoside and methyl β-D-galactopyranoside bound on O-6 to a copolystyrene-DVB resin through a trityl ether linker, have been regioselectively acylated with benzoyl chloride after treatment with Bu2SnO and stannylene formation on solid phase. The benzoylation reactions proved to be highly regioselective affording 2-O benzoyl derivatives for glucose and 3-O benzoyl derivatives for galactose and mannose with high yield. (C) 2000 Elsevier Science Ltd.