Chemical and Pharmaceutical Bulletin p. 53 - 62 (1995)
Update date:2022-08-03
Topics:
Fujii
Ogawa
Saito
Kobayashi
Itaya
Date
Okamura
A detailed account is given of the first unequivocal synthesis of adenine 7-oxide (8). The synthesis started with peroxycarboxylic acid oxidation of 3-benzyladenine (6), readily obtainable from adenine (1) by benzylation, and proceeded through nonreductive debenzylation of the resulting 3-benzyladenine 7-oxide (7). The location of the oxygen function in 7 and 8 was confirmed by their chemical reactions including deamination and methylation and by X-ray crystallographic analysis. A UV spectroscopic approach suggested that the neutral species of 8 exists in H2O as an equilibrated mixture of the NO-oxide (8) and N(7)-OH (21) tautomers. Treatment of 6 with 30% aqueous H2O2 in MeOH in the presence of MeCN and KHCO3 at 30°C produced the N(7)-oxide 7 and 7-acetamido-3-benzyladenine (15) in 12% and 1% yields, respectively.
View MoreContact:+86-519-86623222
Address:29F/D, 99 Yanling West Road, Changzhou, Jiangsu, China
Taizhou Sunny Chemical Co.,Ltd
Contact:+86-523-86920899 +86-13951172783
Address:No.11 Xingyuang road, Gaoyong Chemical Industry Park, Gaogang Jiangsu China
Hebei Kangtai Pharmaceutical Co.,Ltd
Contact:+86-0317-3512963
Address:Wugang Road,Mengcun of Cangzhou City,Hebei Province ,China
Landz International Company Ltd.
Contact:0086-21-58891610
Address:985 Dongfang Road, Pudong, Shanghai 200122 China
Shandong Jiulong Hisince Pharmaceutical Co.,Ltd.
Contact:+86-15853188990
Address:Huadian Pioneer Park, Huadian Township, Qihe County, Dezhou City, Shandong, P.R.China
Doi:10.1016/S0040-4020(01)89387-X
(1994)Doi:10.1002/chem.201405712
(2015)Doi:10.1016/S0040-4039(00)76893-6
(1994)Doi:10.1002/prac.19943360418
(1994)Doi:10.1007/s13738-020-01920-3
(2020)Doi:10.1039/c3ob42422g
(2014)