Mildred L Dulin, L. Noecker, W. Kassel
May 1, 2003
Citations
0
Influential Citations
6
Citations
Journal
Carbohydrate research
Abstract
Bromine activation of phenyl 4-O-acetyl-2,3,6-trideoxy-3-C-methyl-3-trifluoroacetamido-1-thio-alpha,beta-L-ribo-hexopyranoside and attempted coupling with an acceptor in the presence of silver silicate gave an unusual bicyclic product, 2-trifluoromethyl-(4-O-acetyl-2-bromo-2,3,6-trideoxy-3-C-methyl-alpha-L-altrohexopyrano)-[3,2,1-d,e]-2-oxazine, instead of the expected disaccharide. Detailed investigation supported by X-ray crystallographic analysis showed that a trans dibromide is an intermediate in this reaction and that the dibromide is likely formed from a glycal that is generated by elimination during the coupling step.