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2005
Carbohydrates
U 0500
A Straightforward and Flexible [4 + 2] Route to β-C-Naphthyl-2-deoxy-glycosides
Tandem Hydroboration-Ketal Reduction: De Novo Access to
34- 254 Through
C-Naphthyl-6-fluoro and 6,6-Difluoro 2-Deoxyglycosides. — Treatment of dihydropyrans of type (I) with BH3 followed by reaction with H2O2/NaOH results in formation of β-C-alkyl-2-deoxyglycosides via an unprecedented tandem hydroboration-ketal
reduction. Based on this method the first synthesis of the biologically interesting
6-fluoro-2-deoxyglycosides (VI) and (IX) is described. — (VU, N. Q.; LECONTE, S.;
BROWN, E.; GREE, D.; GREE, R.; DUJARDIN*, G.; J. Org. Chem. 70 (2005) 7,
2641-2650; Lab. Chim. Org. Macromol., CNRS, Univ. Maine, F-72085 Le Mans, Fr.;
Eng.) — Jannicke
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