Stereospecific debenzylative cycloetherification of carbohydrate-derived allylic alcohols, ethers and esters to form vinyl C-furanosides

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 tetr...

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Veröffentlicht in:Chemical communications (Cambridge, England) England), 2008-03 (10), p.1246-1248
Hauptverfasser: Cribiù, Riccardo, Cumpstey, Ian
Format: Artikel
Sprache:eng
Schlagworte:
Carbohydrates - chemistry
Cyclization
Esters - chemistry
Ethers - chemistry
Furans - chemistry
Magnetic Resonance Spectroscopy
Propanols - chemistry
Stereoisomerism
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Zusammenfassung: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.
ISSN:1359-7345
1364-548X
DOI:10.1039/b718060h