Stereospecific debenzylative cycloetherification of carbohydrate-derived allylic alcohols, ethers and esters to form vinyl C-furanosides.
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.
Cribiù
Riccardo
R
Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Stockholm, Sweden.
Cumpstey
Ian
I
D002241:Carbohydrates / Q000737:chemistry*; D003500:Cyclization; D004952:Esters / Q000737:chemistry*; D004987:Ethers / Q000737:chemistry*; D005663:Furans / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D020005:Propanols / Q000737:chemistry*; D013237:Stereoisomerism
D002241:Carbohydrates; D004952:Esters; D004987:Ethers; D005663:Furans; D020005:Propanols; C006463:allyl alcohol