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.
All Science Journal Classification (ASJC) codes
- Physical and Theoretical Chemistry
- Organic Chemistry
- Inorganic Chemistry