2-amino-9-[(2R)-4-{[tert-butyl(diphenyl)silyl]oxy}-2-(hydroxymethyl)butyl]-1,9-dihydro-6H-purin-6-one -Drug Synthesis Database

【结构式】

【分子编号】52966

【品名】2-amino-9-[(2R)-4-{[tert-butyl(diphenyl)silyl]oxy}-2-(hydroxymethyl)butyl]-1,9-dihydro-6H-purin-6-one

【CA登记号】

【分子式】C₂₆H₃₃N₅O₃Si

【分子量】491.66542

【元素组成】C 63.52% H 6.77% N 14.24% O 9.76% Si 5.71%

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：(XIV)

In an alternative method, (R)-9-[4-hydroxy-2-(hydroxymethyl)]guanine (VI) was selectively silylated at the 4-hydroxyl by means of tert-butyldiphenylsilyl chloride. The resultant mono-silylated compound (XIV) was acylated with stearoyl chloride (IX), producing stearate ester (XV). Desilylation of (XV) with tetrabutylammonium fluoride, followed by coupling with either N-Boc-L-valine (VII) or N-Cbz-L-valine (XVI), furnished the respective N-protected valyl esters (X) and (XIII). The title compound was then obtained by N-deprotection of (X) and (XIII) under acidic conditions or by catalytic hydrogenation, respectively.

参考文献中间体

合成目标

【1】 Engelhardt, P.; Hoberg, M.; Zhou, X.-X.; Lindborg, B.; Johansson, N.G. (Medivir AB); Acyclic nucleoside derivs.. EP 0888348; JP 2000504720; JP 2000504721; US 5869493; WO 9730051; WO 9730052 .
【2】 Synthesis of acyclic nucleoside derivs.. WO 9834917 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(VI)	52959	2-amino-9-[(2R)-4-hydroxy-2-(hydroxymethyl)butyl]-1,9-dihydro-6H-purin-6-one		C₁₀H₁₅N₅O₃	详情	详情
(VII)	19733	(2S)-2-[(tert-butoxycarbonyl)amino]-3-methylbutyric acid		C₁₀H₁₉NO₄	详情	详情
(IX)	52961	n-Octadecanoyl chloride; Octadecanoyl Chloride; Stearic acid chloride; Stearoyl chloride	112-76-5	C₁₈H₃₅ClO	详情	详情
(X)	52962	(2R)-2-[(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)methyl]-4-({(2S)-2-[(tert-butoxycarbonyl)amino]-3-methylbutanoyl}oxy)butyl stearate		C₃₈H₆₆N₆O₇	详情	详情
(XIII)	52965	(2R)-2-[(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)methyl]-4-[((2S)-2-{[(benzyloxy)carbonyl]amino}-3-methylbutanoyl)oxy]butyl stearate		C₄₁H₆₄N₆O₇	详情	详情
(XIV)	52966	2-amino-9-[(2R)-4-{[tert-butyl(diphenyl)silyl]oxy}-2-(hydroxymethyl)butyl]-1,9-dihydro-6H-purin-6-one		C₂₆H₃₃N₅O₃Si	详情	详情
(XV)	52967	(2R)-2-[(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)methyl]-4-{[tert-butyl(diphenyl)silyl]oxy}butyl stearate		C₄₄H₆₇N₅O₄Si	详情	详情
(XVI)	18092	(2S)-2-[[(benzyloxy)carbonyl]amino]-3-methylbutyric acid		C₁₃H₁₇NO₄	详情	详情

Extended Information