Haiyang Huang, Zhizhong Ruan, T. Hu
2014
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0
Influential Citations
2
Citations
Journal
Chinese Journal of Organic Chemistry
Abstract
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].