Stereoselective synthesis of 1,2:4,5-di-O-isopropylidene-3-C-(5-phenyl-1,2,4-oxadiazol-3-yl)-beta-D-psicopyranose and its X-ray crystallographic analysis.
In a novel procedure, when 3-O-benzoyl-3-C-(N-hydroxycarbamimidoyl)-1,2:4,5-di-O-isopropylidene-beta-D-psicopyranose (1) is treated with acetic anhydride, chloroacetyl chloride, propanic anhydride and benzoyl chloride, the 3-O-benzoyl group undergoes an intramolecular replacement reaction with neighbouring group participation and transfer resulting in a more stable conjugated system by the formation of a 1,2,4-oxadiazol ring. A possible mechanism is reported. The structure has been determined by spectroscopic data and X-ray crystallographic analysis.
Yu
Jianxin
J
Department of Chemistry, Xinjiang University, Wulumqi 830046, China. jian-xin.yu@utsouthwestern.edu
Zhang
Suna
S
Li
Zhongjun
Z
Lu
Wenjie
W
Zhou
Rong
R
Liu
Yuting
Y
Cai
Mengshen
M
D018360:Crystallography, X-Ray; D005632:Fructose / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010069:Oxadiazoles / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
C478180:1,2-4,5-di-O-isopropylidene-3-C-(5-phenyl-1,2,4-oxadiazol-3-yl)-beta-D-psicopyranose; D010069:Oxadiazoles; D005632:Fructose