Journal of Organic Chemistry p. 1794 - 1801 (1987)
Update date:2022-07-29
Topics:
Davisson, V. Jo
Davis, Darrell R.
Dixit, Vyas M.
Poulter, C. Dale
Procedures are described for the synthesis of nucleoside 5'-diphosphates, methanediphosphonates, and difluoromethanediphosphonates.The general strategy involves protection of the nucleosides as amidine, 2',3'-methoxymethylidene, and 3'-(tert-butyldimethylsilyl) derivatives prior to tosylation with tosyl chloride and (N,N-dimethylamino)pyridine.Deprotection, followed by displacement of the tosyl moiety with the tris(tetra-n-butylammonium) pyrophosphate, methanediphosphonate, or difluoromethanediphosphonate salts gave the desired products.The ammonium salts of the nucleotides were purified by flash chromatography on cellulose or medium pressure ion-exchange chromatography on DEAE Fractogel.Syntheses are reported for UDP (18), CDP (19), TDP (20), GDP (21), ADP (23), 2',3'-isopropylidene-ADP (22), adenosine 5'-methanediphosphonate (24), adenosine 5'-difluoromethanediphosphonate (25), and deoxyadenosine 5'-methanediphosphonate (27).In addition ATP (26) was prepared by treatment of 5'-O-tosyladenosine with tetrakis(tetra-n-butylammonium) thiophosphate.Yields for the displacement reactions ranged from 43percent to 93percent.
View MoreSuzhou Kangrun Pharmaceutical, Inc
Contact:86-512-63912376,63913329
Address:Building 2, No. 2358 ,Chang'an Rd, Wujiang Economic Development Zone Pioneering park, china
Shandong Shouguang Songchuan Industrial Additives Co.,Ltd
Contact:+86-536-8566856
Address:Shouguang,Shandong,China
Shandong Shouguang Songchuan Industrial Additives Co.,Ltd
Contact:+86-536-8566856
Address:Shouguang,Shandong,China
Feis International Trade Co,. Ltd
Contact:13961823444-18235944442
Address:Wuxi jiangsu
Taixing Joxin Bio-tec Co.,Ltd.
website:http://www.joxbio.com
Contact:86-523-87558858 87612088
Address:No.88, chengdong industrial park
Doi:10.1016/S0040-4020(01)98444-3
(1964)Doi:10.1002/anie.201810757
(2018)Doi:10.1021/acs.orglett.6b02809
(2016)Doi:10.1021/jo00386a017
(1987)Doi:10.1007/BF01164294
(1988)Doi:10.1021/jo200968f
(2011)