Novel carbohydrate-based mono- and bidentate oligosilyl ethers

Anke Flemming, Constantin Mamat, Martin Köckerling, Clemens Krempner, Ralf Miethchen

Research output: Contribution to journalArticle

6 Scopus citations

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.

Original languageEnglish
Pages (from-to)2685-2692
Number of pages8
JournalSynthesis
Issue number16
DOIs
StatePublished - Aug 17 2006

Keywords

  • Bridging protecting groups
  • Carbohydrates
  • Hydrodesilylation
  • Silyl triflates

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    Flemming, A., Mamat, C., Köckerling, M., Krempner, C., & Miethchen, R. (2006). Novel carbohydrate-based mono- and bidentate oligosilyl ethers. Synthesis, (16), 2685-2692. https://doi.org/10.1055/s-2006-942478