4097-22-7Relevant articles and documents
A MILD CONVERSION OF VICINAL DIOLS TO ALKENES. EFFICIENT TRANSFORMATION OF RIBONUCLEOSIDES INTO 2'-ENE AND 2',3'-DIDEOXYNUCLEOSIDES
Robins, Morris J.,Hansske, Fritz,Low, Nicholas H.,Park, Ja In
, p. 367 - 370 (1984)
α-Acetoxyisobutyryl bromide in "moist" acetonitrile converted adenosine to trans-3'(2')-bromo-2'(3')-acetates with 3percent glycosyl cleavage.This mixture was acetylated, treated with Zn/Cu/DMF, and deacylated to give 81percent of the 2'-alkene.
A stent green synthesis method (by machine translation)
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Paragraph 0026; 0029; 0032; 0033; 0035; 0036; 0038, (2018/10/11)
The invention discloses a stent green synthesis method. The invention to a wide variety of sources adenosine as the starting material, passes through the cyclization, open-loop, catalytic hydrogenation - alkaline hydrolysis, adopts the steps are less, the obtained few by-products, and improves the yield, and reduces the production cost. (by machine translation)
An effective and convenient synthesis of cordycepin from adenosine
Huang, Shen,Liu, Hui,Sun, Yanhua,Chen, Jian,Li, Xiufang,Xu, Jiangfeng,Hu, Yuwei,Li, Yuqing,Deng, Zhiwei,Zhong, Shian
, p. 149 - 160 (2018/01/17)
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%.
Continuous flow photochemistry for the rapid and selective synthesis of 2′-deoxy and 2′,3′-dideoxynucleosides
Shen, Bo,Jamison, Timothy F.
, p. 157 - 164 (2013/04/10)
A new photochemical flow reactor has been developed for the photo-induced electron-transfer deoxygenation reaction to produce 2′-deoxy and 2′,3′-dideoxynucleosides. The continuous flow format significantly improved both the efficiency and selectivity of the reaction, with the streamlined multi-step sequence directly furnishing the highly desired unprotected deoxynucleosides.
