Sugar enolones, XVIII. stereocontrolled functionalization at proanomeric centres by photobromination.–A novel efficient access to oxo??and oximinoglycosyl bromides

FW Lichtenthaler, P Jarglis…

Index: Lichtenthaler, Frieder W.; Jarglis, Pan; Hempe, Walter Liebigs Annalen der Chemie, 1983 , # 11 p. 1959 - 1972

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Abstract

Abstract Suitably O-blocked monosaccharides carrying an electron acceptor group such as an oxo or oximino function next to a proanomeric centre, readily homolyze the corresponding push-pull-substituted C–H bond to give under photobromination conditions the respective α-glycosyl bromides in high yields and virtually stereospecific reactions. Accordingly, the tri-O-benzoyl derivatives of 1, 5-anhydro-D-fructose (7) and the anomeric ...