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Citation: Zhang Pingzhu, Liu Huan, Wei Xiao, Ma Chen, Wang Qiwei, Li Xiaoliu. Synthesis of C-Glycosides Ribosyl-Acid and Ribosyl-Aldehyde[J]. Chinese Journal of Organic Chemistry, ;2016, 36(7): 1690-1695. doi: 10.6023/cjoc201602003 shu

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

1.
Key Laboratory of Chemical Biology of Hebei Province, School of Chemistry and Environmental Science, Hebei University, Baoding 071002

Corresponding author: Li Xiaoliu,
Received Date: 1 February 2016
Revised Date: 9 March 2016

Fund Project: the National Natural Science Foundation of China 21172051the National Natural Science Foundation of China 21372059

Figures(4)

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.
- C-glycosides,
- Wittig-Michael addition,
- ribosyl-acid,
- aldehyde,
- azides
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