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 Morewebsite:http://www.weichichem.com
Contact:+8613912949432
Address:Fine Chemical Industrial Base,Wujiang town,He County,Anhui China.
Contact:86-21-50966856
Address:Building 5,300 Chuanzhan Road,Pudong New District,Shanghai
Changsha Huajing Powdery Material Technological Co., Ltd.
Contact:86-731-88879686
Address:Building 2, West Garden, Main Campus of Central South University, Changsha, Hunan Province, China
zhenjiang runjing high purity chemical co ltd
Contact:+86-511-83361155
Address:No.8.haixi road,international chemical park
Contact:86-931-8272767
Address:Room 602, No.461, Nanchang Road, Chengguan District, Lanzhou City, China PRC
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)
