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Chinese Journal of Organic Chemistry >

2016 , Vol. 36 >Issue 7: 1690 - 1695

DOI: https://doi.org/10.6023/cjoc201602003

Notes

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

  • Zhang Pingzhu ,
  • Liu Huan ,
  • Wei Xiao ,
  • Ma Chen ,
  • Wang Qiwei ,
  • Li Xiaoliu
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  • Key Laboratory of Chemical Biology of Hebei Province, School of Chemistry and Environmental Science, Hebei University, Baoding 071002

Received date: 2016-02-01

  Revised date: 2016-03-09

  Online published: 2016-03-18

Supported by

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

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Abstract

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

Cite this article

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

References

[1] (a) Varki, A.; Cummings, R.; Esko, J.; Freeze, H.; Hart, G.; Marth, J. Essentials of Glycobiology, Lajolla, California, 2002, p. 57.
(b) Science, 2001, 291(5512), the all articles.
(c) Nature, 2007, 446(7139), the all articles.
[2] (a) Fraser-Reid, B. O.; Tatsuta, K.; Them, J. Glycoscience: Chemistry and Chemical Biology, 2nd ed., Springer, Berlin, 2008.
(b) Wong, C. H. Carbohydrate-based Drug Discovery, WILEY- VCH, Weinheim, 2003.
[3] (a) Zou, W. Curr. Top. Med. Chem. 2005, 5(14), 1297.
(b) Wang, J.; Kovác, P.; Sinäy, P.; Glaudemans, P. J. Carbohydr. Res. 1998, 308, 191.
[4] (a) Lalithaa, K.; Muthusamya, K.; Siva Prasada, Y.; Vemulab, P. K.; Nagarajana, S. Carbohydr. Res. 2015, 402, 158.
(b) Clercq, E. D. J. Med. Chem. 2016, 59, 2301.
(c) Hocek, M.; Pavel, K.; Stambaský, J. Chem. Rev. 2009, 109, 6729.
(d) Moos, E. v.; Ben, R. N. Curr. Top. Med. Chem. 2005, 5(14), 1351.
[5] (a) Postema, M. H. D. Tetrahedron 1992, 48, 8545.
(b) Liu, L.; McKee, M.; Postema, M. H. D. Curr. Org. Chem. 2001, 5, 1133.
[6] von Itzstein, M.; Taylor, N. R. J. Med. Chem. 1994, 37, 616.
[7] Ma, D. L.; Li, X. L.; Hao, L.; Zhang, P. Z.; Chen, h.; Zhao, Y. Chem. J. Chin. Univ. 2014, 355, 959 (in Chinese). (马东来, 李小六, 郝乐, 张平竹, 陈华, 赵影, 高等学校化学学报, 2014, 355, 959.)

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