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Synlett 2009(7): 1154-1156
DOI: 10.1055/s-0028-1088105
DOI: 10.1055/s-0028-1088105
LETTER
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of 2,3-Unsaturated O- and N-Glycosides by HBF4˙SiO2-Catalyzed Ferrier Rearrangement of d-Glycals
Weitere Informationen
Publikationsverlauf
Received
1 January 2009
Publikationsdatum:
20. März 2009 (online)


Abstract
Fluoroboronic acid adsorbed on silica gel (HBF4˙SiO2) catalyzes the Ferrier rearrangement of per-O-acetylated glycals with alcohols and sulfonamides to give 2,3-unsaturated O- and N-glycosides in good to excellent yield and with high α-stereoselectivity.
Key words
glycosylations - green chemistry - Ferrier rearrangement - N-glycosylsulfonamides - O-glycosides