(20R,24R)-epoxy-dammar-3β,6α,12β,25-tetraol (1) and (20R,24S)-epoxy- dammar-3β, 6α,12β,25-tetraol (2) have been synthesized from 20(R)-protopanaxatriol with same polarity. In order to obtain optically pure 1 and 2, (20R,24R)-3,6-diacetyl- 20,24-epoxydammar-3β,6α,12β,25-tetraol (3) and (20R,24S)-3,6-diacetyl-20,24- epoxydammar-3β,6α,12β,25-tetraol (4) were designed and prepared to enhance the polarity difference of C24 epimers. Two suitable crystals of 3 and 4 were obtained and their structures were determined by 1H NMR, 13C NMR, HR-MS and X-ray single-crystal diffraction. The results indicated that the C-24 configuration of 3 and 4 are R-form and S-form, respectively. 3 has two intramolecular hydrogen bond. While there is only one in 4 and the crystal stacking displays that it generates a right-handed helically chiral channel viewing from the crystallographic b axis via classical O–H•••O intermolecular hydrogen bond.


Juan Liu, Wen-Zhi Wang, Jia-Zhen Wang, Gui-Ge Hou, Qing-Guo Meng