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  • Title: Stereospecific debenzylative cycloetherification of carbohydrate-derived allylic alcohols, ethers and esters to form vinyl C-furanosides.
    Author: Cribiù R, Cumpstey I.
    Journal: Chem Commun (Camb); 2008 Mar 14; (10):1246-8. PubMed ID: 18309432.
    Abstract:
    Benzyl ether protected polyhydroxylated alkene compounds containing allylic alcohol, ether or ester functionality undergo a stereospecific cyclisation reaction upon treatment with TFA-acetonitrile-toluene with inversion of configuration at the allylic position and loss of a benzyl ether to give tetrahydrofurans.
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