Synthesis and elimination of C-3-labeled thiosialosides.
The synthesis of C-3-labeled phenylthio sialic acid derivatives and an investigation of stereoselectivity in elimination reactions for the synthesis of 2,3-dehydro derivatives (glycals) is described. The experimental results are consistent with the existence of a conformational change and may be indicative of the intermediacy of an all-axial oxacarbenium ion.
Department of Chemistry, Southern Illinois University Edwardsville , Edwardsville, Illinois 62026, United States.
Cristina
C
De Meo
Clare E
CE
Wallace
Scott A
SA
Geringer
D015394:Molecular Structure; D012794:Sialic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013457:Sulfur Compounds / Q000138:chemical synthesis* / Q000737:chemistry
D012794:Sialic Acids; D013457:Sulfur Compounds