TY - JOUR
T1 - C-Arylglucoside synthesis
T2 - Triisopropylsilane as a selective reagent for the reduction of an anomeric C-phenyl ketal
AU - Ellsworth, Bruce A.
AU - Doyle, Abigail G.
AU - Patel, Manorama
AU - Caceres-Cortes, Janet
AU - Meng, Wei
AU - Deshpande, Prashant P.
AU - Pullockaran, Annie
AU - Washburn, William N.
N1 - Copyright:
Copyright 2008 Elsevier B.V., All rights reserved.
PY - 2003/10/17
Y1 - 2003/10/17
N2 - 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.
AB - 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.
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U2 - 10.1016/j.tetasy.2003.08.007
DO - 10.1016/j.tetasy.2003.08.007
M3 - Article
AN - SCOPUS:1642406208
SN - 0957-4166
VL - 14
SP - 3243
EP - 3247
JO - Tetrahedron Asymmetry
JF - Tetrahedron Asymmetry
IS - 20
ER -