Journal of Organic Chemistry p. 1294 - 1298 (1988)
Update date:2022-08-05
Topics:
Garner, Philip
Ramakanth, Sarabu
The reaction of 2-O-acetylated and 2-O-benzoylated glycosides 3a,b/4a,b with silylated N2-acetylguanine 7 selectively gave N7-guanine nucleosides 8a,b/9a,b under kinetically controlled conditions (SnCl4/CH3CN, room temperature), whereas 2-O-benzoylated glycosides 3b/4b selectively gave isomeric N9-guanine nucleosides 10b/11b under termodynamically controlled conditions (TMSOTf/(CH2Cl)2, reflux).Unambiguous assignment of nucleoside structure was accomplished after hydrolysis (NH3/MeOH) of the initial products to the known nucleosides 8c, 9c, 10c, and 11c followed by 1H NMR and 13C NMR spectral analysis.The described procedures provide the best method to date for the selective synthesis of either N7- or N9-guanine nucleosides from a common substrate.
View MoreHangzhou Yingshanhua Pigment Chemicals Co.,Ltd.
Contact:+86-0150-58101658
Address:Nanyang Economic DevelopmentZong,Xiaoshan,Hangzhou,China
Liaoyang Xinyou Chemical Products Co.,Ltd.
Contact:+86-419-5165433 13604191870
Address:Huishang Road6-1, Hongwei District, Liaoyang, Liaoning, China
Contact:+86 21 34123252
Address:14, 4580 Dushi, Shanghai, China
Beijing Greenchem Technology Co.,Ltd. ( Panjin Greenchem Technology Co.Ltd .)
website:http://www.bjgreenchem.com/
Contact:+86-427-6515887
Address:301,302, 3rd Floor, Building C-7, Dongsheng Science Park, Northern Territory, Zhongguancun, No. 66, Xixiaokou Road, Haidian District, Beijing
Zhangjiagang Golden Reach Fine Chemical Co.,LTD.
Contact:+86-512-6585 6968
Address:Changfu Road, Dongsha Chemical Industry Park, Zhangjiagang City, Jiangsu Province, China
Doi:10.1007/s10895-010-0782-2
(2011)Doi:10.1002/hlca.19840670832
(1984)Doi:10.1021/ja01160a073
(1950)Doi:10.1039/jr9330001628
(1933)Doi:10.1039/JR9490002948
()Doi:10.1021/jo01358a017
(1957)