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

doi:10.1016/j.tetasy.2003.08.007

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 journal › Article › peer-review

42 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 language	English (US)
Pages (from-to)	3243-3247
Number of pages	5
Journal	Tetrahedron Asymmetry
Volume	14
Issue number	20
DOIs	https://doi.org/10.1016/j.tetasy.2003.08.007
State	Published - Oct 17 2003

All Science Journal Classification (ASJC) codes

Catalysis
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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@article{c924851581f34384a650fbd3fa3919ac,

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

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.",

author = "Ellsworth, \{Bruce A.\} and Doyle, \{Abigail G.\} and Manorama Patel and Janet Caceres-Cortes and Wei Meng and Deshpande, \{Prashant P.\} and Annie Pullockaran and Washburn, \{William N.\}",

year = "2003",

month = oct,

day = "17",

doi = "10.1016/j.tetasy.2003.08.007",

language = "English (US)",

volume = "14",

pages = "3243--3247",

journal = "Tetrahedron Asymmetry",

issn = "0957-4166",

publisher = "Elsevier Ltd",

number = "20",

}

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.

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.

UR - https://www.scopus.com/pages/publications/1642406208

UR - https://www.scopus.com/pages/publications/1642406208#tab=citedBy

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 -

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

Abstract

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