ISSN print edition: 0366-6352
ISSN electronic edition: 1336-9075
Registr. No.: MK SR 9/7
An effective and convenient synthesis of cordycepin from adenosine
Shen Huang, Hui Liu, Yanhua Sun, Jian Chen, Xiufang Li, Jiangfeng Xu, Yuwei Hu, Yuqing Li, Zhiwei Deng, and Shian Zhong
Central South University, Changsha, China
Abstract: Cordycepin is a purine nucleoside analog with potent and diverse biological activities. Herein, we designed two methods to synthesize cordycepin. One method mainly converted the 3′-OH group into an iodide group and further dehalogenation to yield the final product. Although this method presented a short synthetic procedure, the synthesis had a low overall yield, resulting in only 13.5% overall yield. To improve the overall yield of cordycepin, another synthetic route was studied, which consisted of four individual steps: (1) 5′-OH protection (2) esterification (3) -O-tosyl (-OTs) group removal (4) deprotection. The key step in the synthetic method involved the conversion of 5′-O-triphenylmethyladenosine to 3′-O-tosyl-5′-O-triphenylmethyladenosine, using LiAlH4 as reducing agent. The main advantages of this route were an acceptable total product yield and the commercial availability of all starting materials. The optimal reaction conditions for each step of the route were identified. The overall yield of cordycepin obtained from adenosine as the starting material was 36%.
Keywords: Adenosine ; Deoxyadenosine ; Cordycepin ; Synthesis
Full paper is available at www.springerlink.com.
Chemical Papers 72 (1) 149–160 (2018)