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 hav...

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Bibliographic Details
Published in:Tetrahedron 2000-08, Vol.56 (35), p.6511-6516
Main Authors: Barros, M.Teresa, Maycock, Christopher D., Siñeriz, Fernando, Thomassigny, Christine
Format: Article
Language:English
Subjects:
gallotannins
galloylation
sucrose
tert-butyldiphenylsilyl ether (deprotection of)
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Summary: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.
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(00)00593-7