Dibutyl tin oxide mediated, regioselective alkylation and acylation of siloxane protected glycopyranosides

Article abstract of DOI:10.1055/s-1999-3569

Treatment of alkyl and aryl 4,6-O-(1,1,3,3-tetraisopropyl-1,3- disiloxane-1,3-diyl)-D-glycopyranosides 2 with dibutyltin oxide followed by benzoyl chloride, benzyl bromide and allyl bromide afforded regioselectively the corresponding mono acylated and alkylated glycosides. The regioselective acylation of the stannylene intermediates is inverted as compared to the direct acylation of 2. Regioselective alkylations of 2 proceeded without affecting the siloxane residue.