有机化学 ›› 2014, Vol. 34 ›› Issue (7): 1358-1363.DOI: 10.6023/cjoc201402027 上一篇    下一篇

研究论文

杀结核菌素的全合成研究

黄海洋, 阮志忠, 胡韬, 肖强   

  1. 江西科技师范大学有机功能分子研究所 南昌 330013
  • 收稿日期:2014-02-23 修回日期:2014-03-20 发布日期:2014-04-10
  • 通讯作者: 肖强 E-mail:xiaoqiang@tsinghua.org.cn
  • 基金资助:

    国家自然科学基金(Nos.20962009,21062006)、教育部新世纪优秀人才支持计划(No.11-1000)、江西省青年科学家培养对象项目和南昌市科技局资助项目.

An Improved Total Synthesis of Tubercidin

Huang Haiyang, Ruan Zhizhong, Hu Tao, Xiao Qiang   

  1. Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science & Technology Normal University, Nanchang 330013
  • Received:2014-02-23 Revised:2014-03-20 Published:2014-04-10
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos. 20962009, 21062006), the Program for New Century Excellent Talents in University (No. 11-1000), the Training Project of Jiangxi Youth Scientists and the Bureau of Science & Technology of Nanchang City.

杀结核菌素是一个吡咯[2,3-d]嘧啶核苷天然产物,具有显著的抗血吸虫感染、抗菌和抗肿瘤活性. 报道了以微波促进的Vorbrüggen糖基化反应为关键步骤,以6-氯-7-溴-吡咯[2,3-d]嘧啶和1-O-乙酰基-2,3,5-O-三苯甲酰基-D-呋喃核糖为原料,经过3步反应以74%的总收率完成了杀结核菌素的全合成. 同时研究了以全氟丁基磺酸钾、三甲基氯硅烷和硅基化试剂[六甲基二硅胺烷或者NO-双(三甲基硅基)乙酰胺]在微波加热下一锅法合成7-去氮嘌呤核苷的方法.

关键词: 核苷, 全合成, 天然产物, 糖基化, 微波

Tubercidin is a naturally occurring pyrrolo[2,3-d]pyrimidine nucleoside with significantly biological activities, such as anti-schistosomal, antibacterial and antitumor. An improved total synthesis of tubercidin is reported using microwave promoted Vorbrüggen glycosylation as the key step. Thus, tubercidin was synthesized in 3 steps with 74% overal yield using 6-chloro-7-bromo-pyrrolo[2,3-d]pyrimidine and 1-O-acetyl-2,3,5-O-tribenzoyl-β-D-ribose as starting materials. The applica- tion of micromave irridated one-pot reaction is also reported in the synthesis of 7-deazapurine nucleosides using potassium nonafluoro-1-butanesulfonate, trimethylsilyl chloride and silylation reagent [hexamethyldisilazane or N,O-bis(trimethyl- silyl)acetamide].

Key words: nucleoside, total synthesis, natural product, glycosylation, microwave