Volume 31, Issue 34
Natural Products
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ChemInform Abstract: Organocopper Reagents (RCu, R2CuLi) for the Nucleophilic C-Glycosylation of a C(2)-Formyl Glycal.

Janine Cossy

Janine Cossy

Lab. Chim. Org., CNRS, Ec. Super. Phys. Chim. Ind., F-75231 Paris, Fr.

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Haja Rakotoarisoa

Haja Rakotoarisoa

Lab. Chim. Org., CNRS, Ec. Super. Phys. Chim. Ind., F-75231 Paris, Fr.

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First published: 03 June 2010

Abstract

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ChemInform Abstract

SN2′-Reaction of the C(2)-formyl glycal (I) with alkylcopper reagents in the presence of BF3×OEt2 or analogous 1,4-addition of (I) with lithium dialkylcuprate provides a stereoselective formation of C(1)-glycosides (III) and (V)/(VI), respectively.

chemical structure image

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