Tetrahedron

On the synthesis of vinyl and phenyl C-furanosides by stereospecific debenzylative cycloetherification

R Cribiù, KE Borbas, I Cumpstey

Index: Cribiu, Riccardo; Eszter Borbas; Cumpstey, Ian Tetrahedron, 2009 , vol. 65, # 10 p. 2022 - 2031

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Citation Number: 15

Abstract

Open-chain benzyl-ether-protected polyols in which one of the alcohols is either allylic or benzylic are synthesised by addition of organometallic vinyl or phenyl reagents to benzyl- ether-protected carbohydrate hemiacetals. The diastereoselectivity of addition is dependent on whether a Grignard reagent or a trialkylzincate reagent is used. The open-chain compounds undergo a stereospecific cyclisation reaction on treatment with catalytic strong ...