An Improved Total Synthesis of Tubercidin

作者：Huang Haiyang^*; Ruan Zhizhong; Hu Tao; Xiao Qiang

来源：Chinese Journal of Organic Chemistry, 2014, 34(7): 1358-1363.

DOI：10.6023/cjoc201402027

• nucleoside
• total synthesis
• natural product
• glycosylation
• microwave

Tubercidin is a naturally occurring pyrrolo[2,3-d]pyrimidine nucleoside with significantly biological activities, such as anti-schistosomal, antibacterial aid antitumor. An improved total synthesis of tubercidin is reported using microwave promoted Vorbruggen 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-beta-D-ribose as starting materials. The application of micromave irridated one-pot reaction is also reported in the synthesis of 7-deazapurine nucleosides using potassium nonafluoro-l-butanesulfonate, trimethylsilyl chloride and silylation reagent [hexamethyldisilazane or N,O-bis(trimethylsilyl)acetamide].

• 出版日期2014-7
• 单位江西科技师范大学