Synthesis 2006(16): 2685-2692  
DOI: 10.1055/s-2006-942478
PAPER
© Georg Thieme Verlag Stuttgart · New York

Novel Carbohydrate-Based Mono- and Bidentate Oligosilyl Ethers

Anke Flemming, Constantin Mamat, Martin Köckerling, Clemens Krempner*, Ralf Miethchen*
Institut für Chemie, Universität Rostock, Albert-Einstein-Straße 3a, 18059 Rostock, Germany
Fax: +49(381)4986412; e-Mail: ralf.miethchen@uni-rostock.de;
Further Information

Publication History

Received 17 March 2006
Publication Date:
11 July 2006 (eFirst)

Abstract

Regioselective one-pot O-silylation reactions of 1,2-O-isopropylidene-α-d-glucofuranose and 1,2-O-isopropylidene-β-d-fructopyranose using bulky oligosilyl groups are described. Some new silylating reagents (oligosilyl bistriflates), which were generated in situ from readily available phenylsilanes, resulted in 5,6-O-(glucofuranose) and 4,5-O-bridged (fructopyranose) carbohydrates with favoured seven- and eight-membered rings. In these cyclic oligosilyl diethers, three and four ring atoms, respectively, are Si atoms. It is noteworthy, that the seven-membered ring of 5,6-O-[2,4-bis(trimethylsilyl)-1,1,1,3,3,5,5,5-octamethylpentasilan-2,4-diyl]-1,2-O-isopropylidene-α-d-glucofuranose was expanded to an eight-membered ring by regioselective insertion of aerial oxygen into one of the Si-Si bonds. X-ray analyses of some derivatives are presented.

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