Stereoselective synthesis, structural characterization, and properties of 1,2-O-isopropylidene-3-C-(5-phenyl-1,2,4-oxadiazol-3-yl)-beta-D-psicopyranose.
1,2:4,5-Di-O-isopropylidene-3-C-(5-phenyl-1,2,4-oxadiazol-3-yl)-beta-D-psicopyranose 14 was synthesized stereoselectively from 1,2:4,5-di-O-isopropylidene-3-C-amidoximino-3-O-benzoyl-beta-D-psicopyranose 8 using a novel procedure. Treatment of 8 with acetic anhydride, chloroacetyl chloride, propanic anhydride, or benzoyl chloride causes the 3-O-benzoyl group to undergo an intramolecular replacement reaction with neighboring group participation and transfer resulting in a more stable conjugation system of the 1,2,4-oxadiazol ring. A possible mechanism, as well as structural analysis and bioactivity are described.
Yu
Jianxin
J
Advanced Radiological Sciences, Department of Radiology, The University of Texas Southwestern Medical Center at Dallas, 5323 Harry Hines Blvd., Dallas, TX 75390-9058, USA. jian-xin.yu@utsouthwestern.edu
Zhang
Suna
S
Li
Zhongjun
Z
Lu
Wenjie
W
Cai
Mengshen
M
D002236:Carbohydrate Conformation; D008958:Models, Molecular; D015394:Molecular Structure; D009005:Monosaccharides / Q000138:chemical synthesis / Q000737:chemistry*; D010069:Oxadiazoles / Q000138:chemical synthesis / Q000737:chemistry*; D011714:Pyrans / Q000737:chemistry*
C500548:1,2-O-isopropylidene-3-C-(5-phenyl-1,2,4-oxadiazol-3-yl)-beta-D-psicopyranose; D009005:Monosaccharides; D010069:Oxadiazoles; D011714:Pyrans