【结 构 式】 |
【分子编号】64284 【品名】1-{(2R,4S,5S)-4-azido-5-[3-(4-{(2S)-3-[bis(tert-butoxycarbonyl)amino]-2-[(tert-butoxycarbonyl)amino]-3-oxopropyl}phenoxy)-9,9-dimethyl-8-oxo-2,4-dioxa-7-thia-3-phosphadec-1-yl]tetrahydro-2-furanyl}-5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine 【CA登记号】 |
【 分 子 式 】C41H60N7O14PS 【 分 子 量 】938.005942 【元素组成】C 52.5% H 6.45% N 10.45% O 23.88% P 3.3% S 3.42% |
合成路线1
该中间体在本合成路线中的序号:(IX)Tetrazole-catalyzed phosphitylation of the tyrosinamide derivative (V) with O-2-(pivaloylthio)ethyl-N,N,N',N'-tetraisopropylphosphorodiamidite (VI) yields phosphoramidite (VII). This is subsequently coupled to azidothimidine (VIII) to furnish phosphite (IX), which is then oxidized to the corresponding phosphate (X) with t-butyl hydroperoxide. The N-Boc protecting groups of (X) are finally removed under acidic conditions to provide the title compound.
【1】 Peyrottes, S.; Coussot, G.; Lefebvre, I.; Imbach, J.-L.; Gosselin, G.; Aubertin, A.-M.; Perigaud, C.; S-acyl-2-thioethyl aryl phosphotriester derivatives of AZT: Synthesis, antiviral activity, and stability study. J Med Chem 2003, 46, 5, 782. |
中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
---|---|---|---|---|---|---|
(V) | 64281 | (7S)-5-(tert-butoxycarbonyl)-7-(4-{[tert-butyl(dimethyl)silyl]oxy}benzyl)-2,2,11,11-tetramethyl-4,6,9-trioxo-3,10-dioxa-5,8-diazadodecane | C30H50N2O8Si | 详情 | 详情 | |
(VI) | 64282 | S-(2-{[bis(diisopropylamino)phosphino]oxy}ethyl) 2,2-dimethylpropanethioate | C19H41N2O2PS | 详情 | 详情 | |
(VII) | 64283 | (7S)-5-(tert-butoxycarbonyl)-7-{4-[((diisopropylamino){2-[(2,2-dimethylpropanoyl)sulfanyl]ethoxy}phosphino)oxy]benzyl}-2,2,11,11-tetramethyl-4,6,9-trioxo-3,10-dioxa-5,8-diazadodecane | C37H62N3O10PS | 详情 | 详情 | |
(VIII) | 25317 | 1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)tetrahydro-2-furanyl]-5-methyl-2,4(1H,3H)-pyrimidinedione | 101703-35-9 | C10H13N5O4 | 详情 | 详情 |
(IX) | 64284 | 1-{(2R,4S,5S)-4-azido-5-[3-(4-{(2S)-3-[bis(tert-butoxycarbonyl)amino]-2-[(tert-butoxycarbonyl)amino]-3-oxopropyl}phenoxy)-9,9-dimethyl-8-oxo-2,4-dioxa-7-thia-3-phosphadec-1-yl]tetrahydro-2-furanyl}-5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine | C41H60N7O14PS | 详情 | 详情 | |
(X) | 64285 | 1-{(2R,4S,5S)-4-azido-5-[3-(4-{(2S)-3-[bis(tert-butoxycarbonyl)amino]-2-[(tert-butoxycarbonyl)amino]-3-oxopropyl}phenoxy)-9,9-dimethyl-3,8-dioxo-2,4-dioxa-7-thia-3lambda~5~-phosphadec-1-yl]tetrahydro-2-furanyl}-5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine | C41H60N7O15PS | 详情 | 详情 |