2010•European Journal of Organic ChemistryRequires access

Perfectly Regioselective and Sequential Protection of Glucopyranosides

Wataru Muramatsu, Kenji Mishiro, Y. Ueda, Takumi Furuta, Takeo Kawabata

Abstract

Abstract A perfectly regioselective and sequential method for the preparation of orthogonally protected glucopyranosides has been developed. An acyl group was introduced at C(4)‐OH by organocatalysis with >99 % regioselectivity. TBDPS, Boc, and BOM groups were sequentially introduced into the 4‐O‐acyl‐glucopyranoside at C(6)‐OH, C(2)‐OH, and C(3)‐OH, respectively, with ca. 100 % regioselectivity in each step.

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Key concepts: Regioselectivity, Chemistry, Combinatorial chemistry, Stereochemistry, Organic chemistry, Catalysis