Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (7): 1690-1695.DOI: 10.6023/cjoc201602003 Previous Articles     Next Articles

Notes

C-糖苷核糖酸及核糖醛的合成

张平竹, 刘欢, 魏笑, 马趁, 王齐伟, 李小六   

  1. 河北大学化学与环境科学学院 河北省化学生物学重点实验室 保定 071002
  • 收稿日期:2016-02-01 修回日期:2016-03-09 发布日期:2016-03-18
  • 通讯作者: 李小六 E-mail:lixl@hbu.cn
  • 基金资助:

    国家自然科学基金(Nos.21172051,21372059)资助项目.

Synthesis of C-Glycosides Ribosyl-Acid and Ribosyl-Aldehyde

Zhang Pingzhu, Liu Huan, Wei Xiao, Ma Chen, Wang Qiwei, Li Xiaoliu   

  1. Key Laboratory of Chemical Biology of Hebei Province, School of Chemistry and Environmental Science, Hebei University, Baoding 071002
  • Received:2016-02-01 Revised:2016-03-09 Published:2016-03-18
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos. 21172051, 21372059).

For exploring a simple and efficient synthetic method of C-glycosides, (2,3-O-isopropylidene)-β-C-D-ribosyl ethyl acetate and (2,3-O-isopropylidene)-β-C-D-ribosyl acetic acid were stereospecifically synthesized by a one-pot tandem Wittig-Michael addition reaction, and then treated with corresponding base, respectively. The acetates were reduced by DIBAL-H to obtain the corresponding glycosyl aldehyde. D-xylose was treated following the procedure of acetonide of 1,2-position, trifluoroacetoxyation of 3,5-position. The trifluoroacetoxyl groups were substituted by azido groups, followed by the one-pot tandem Wittig-Michael addition reaction, and then treated with corresponding base. 3,5-Diazido-β-C-D-ribosyl acetic acid was obtained in high stereo specificity.

Key words: C-glycosides, Wittig-Michael addition, ribosyl-acid, aldehyde, azides