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2005
Carbohydrates
U 0500
DDQ-Mediated Regioselective de-O-Benzylation of Pyranosides Stilted by
4,6-O-(2-Phenylsulfonyl)ethylidene (PSE) Clip. — A model study on diverse
25- 194 a4,6-acetalized
O-benzylated D-glucopyranosides is performed to evaluate DDQ-mediated regioselective de-O-benzylation in connection with structural rigidity. The
PSE-acetal (III) fully resists DDQ oxidation, while benzyl groups are removed with
fairly regioselective 3-de-O-benzylation. — (CABIANCA, E.; TATIBOUET, A.;
ROLLIN*, P.; Pol. J. Chem. 79 (2005) 2, 317-322; Inst. Chim. Org. Anal., CNRS,
Fac. Sci., Univ. Orleans, F-45067 Orleans, Fr.; Eng.) — A. Forchert
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