Stereoselective synthesis of 9-beta-d-arabianofuranosyl guanine and 2-amino-9-(beta-d-arabianofuranosyl)purine.
9-beta-d-Arabianofuranosyl guanine (6) and 2-amino-9-(beta-d-arabianofuranosyl)purine (8) were prepared from 2-amino-6-chloro-9-(2,3,5-triphenylmethoxyl-beta-d-arabianofuranosyl)purine (4), a key intermediate which was stereoselectively prepared from 2,3,5-triphenylmethoxyl-d-arabianofuranose and 2-amino-6-chloro-purine. The yield of the intermediate was obviously improved and only beta-isomer was formed by using the activated molecular sieve as environmental friendly catalyst, overcoming the defect that a 1:1 mixture of alpha- and beta-isomers was formed, which was difficult to separate, when toxic mercury cyanide was previously used as catalyst.
Yu
Xue-Jun
XJ
Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, PR China. finechem@public2.zz.ha.cn
Li
Gai-Xia
GX
Qi
Xiou-Xiang
XX
Deng
You-Quan
YQ
D019380:Anti-HIV Agents / Q000138:chemical synthesis*; D002384:Catalysis; D006151:Guanosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D015386:Hazardous Substances; D006801:Humans; D011684:Purine Nucleosides / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D019380:Anti-HIV Agents; D015386:Hazardous Substances; D011684:Purine Nucleosides; D006151:Guanosine