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

@inproceedings{Lichtenthaler1983SugarEX,
  title={Sugar enolones, XVIII. stereocontrolled functionalization at proanomeric centres by photobromination. – A novel efficient access to oxo‐ and oximinoglycosyl bromides},
  author={Frieder W. Lichtenthaler and Pan Jarglis and Walter Hempe},
  year={1983}
}
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 L-lyxo-hexos-4-uloses (12, 15) give the α-bromides 8, 13, and 16 in yields… CONTINUE READING

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