C-Arylglucoside synthesis: Triisopropylsilane as a selective reagent for the reduction of an anomeric C-phenyl ketal

Bruce A. Ellsworth, Abigail G. Doyle, Manorama Patel, Janet Caceres-Cortes, Wei Meng, Prashant P. Deshpande, Annie Pullockaran, William N. Washburn

Research output: Contribution to journalArticle

37 Scopus citations

Abstract

Reduction of tetra-O-benzyl-protected 1C-phenylglucoside using triethylsilane and BF3·OEt2 has been reported (Czernecki, S.; Ville, G. J. Org. Chem. 1989, 54, 610-612) to give exclusively 2,3,4,6-tetra-O-benzyl-β-1C-phenyl-1-deoxyglucoside. We have determined that this reduction actually gives a 4:1 mixture of anomers (β:α). We observed that the selectivity of the reduction is influenced by the steric bulk of the silane. The use of triisopropylsilane as a reducing agent gives >35:1 ratio (β:α) of 2,3,4,6-tetra-O-benzyl-β-1C-phenyl-1- deoxyglucoside.

Original languageEnglish (US)
Pages (from-to)3243-3247
Number of pages5
JournalTetrahedron Asymmetry
Volume14
Issue number20
DOIs
StatePublished - Oct 17 2003
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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    Ellsworth, B. A., Doyle, A. G., Patel, M., Caceres-Cortes, J., Meng, W., Deshpande, P. P., Pullockaran, A., & Washburn, W. N. (2003). C-Arylglucoside synthesis: Triisopropylsilane as a selective reagent for the reduction of an anomeric C-phenyl ketal. Tetrahedron Asymmetry, 14(20), 3243-3247. https://doi.org/10.1016/j.tetasy.2003.08.007