S-(2-{[bis(diisopropylamino)phosphino]oxy}ethyl) 2,2-dimethylpropanethioate -Drug Synthesis Database

【结构式】

【分子编号】64282

【品名】S-(2-{[bis(diisopropylamino)phosphino]oxy}ethyl) 2,2-dimethylpropanethioate

【CA登记号】

【分子式】C₁₉H₄₁N₂O₂PS

【分子量】392.586582

【元素组成】C 58.13% H 10.53% N 7.14% O 8.15% P 7.89% S 8.17%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(VI)

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.

参考文献中间体

合成目标

【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

Extended Information