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. (C) 2000 Elsevier Science Ltd. All rights reserved.