Fast Galloylation of a Sugar Moiety: Preparation of Three Monogalloylsucroses as References for Antioxidant Activity. A Method for the Selective Deprotection of tert-Butyldiphenylsilyl Ethers

Three protected new gallotannins, namely the 6′-O-(tri-O-methylgalloyl)-2,3,4,6,1′,3′,4′-hepta-O-acetylsucrose, the 6′-O-(tri-O-methylgalloyl)-2,3,4,6,1′,3′,4′-hepta-O-benzoylsucrose and the 6,6′-di-O-tert-butyldiphenylsilyl-1′-O-(tri-O-methylgalloyl)-2,3,4,3′,4′-penta-O-acetylsucrose have been prepared in four short sequences from sucrose. Methods for rapid galloylation have been studied in order to avoid simultaneous acyl transfer reactions. A method for the deprotection of a tert-butyldiphenylsilyl ether has been developed which avoids the intramolecular migration of a benzoate group.