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有机化学
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有机化学 ›› 2016, Vol. 36 ›› Issue (7): 1690-1695.DOI: 10.6023/cjoc201602003 上一篇    下一篇

研究简报

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).

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补充材料

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为了探讨C-糖苷高效、简便的合成方法，分别以D-核糖和2，3-O-异丙叉基-D-核糖为原料，与膦叶立德进行Wittig-Michael加成串联反应，然后不同碱处理，一锅法高产率立体专一性地合成相应的（2，3-O-异丙叉基）-β-C-D-核糖乙酸乙酯和（2，3-O-异丙叉基）-β-C-D-核糖乙酸； 所得酯经DIBAL-H低温还原，得相应的核糖基醛衍生物； 以D-木糖为原料，经1，2-羟基保护成缩丙酮，3，5-位二羟基三氟甲磺酰基化、叠氮化，1，2-羟基脱保护，然后经与膦叶立德Wittig-Michael加成串联反应，碱处理，高产率、立体专一性地合成了含两个叠氮基的β-C-D-核糖乙酸. 提供了一种C-糖苷及氨基C-糖苷快捷、高效、简便的合成方法. 化合物结构经1H NMR、13C NMR、HRMS等确证.

关键词: 碳苷, Wittig-Michael加成, 糖酸, 糖醛, 叠氮化合物

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