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.
Peri, F., Cipolla, L., Nicotra, F. (2000). Tin-mediated regioselective acylation of unprotected sugars on solid phase. TETRAHEDRON LETTERS, 41(44), 8587-8590 [10.1016/S0040-4039(00)01492-1].
Tin-mediated regioselective acylation of unprotected sugars on solid phase
PERI, FRANCESCO;CIPOLLA, LAURA FRANCESCA;NICOTRA, FRANCESCO
2000
Abstract
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.
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