9-[[2-hydroxy-1-(hydroxymethyl)ethoxy]methyl]-2-[(trimethylsilyl)amino]-1,9-dihydro-6H-purin-6-one -Drug Synthesis Database

【结构式】

【分子编号】35313

【品名】9-[[2-hydroxy-1-(hydroxymethyl)ethoxy]methyl]-2-[(trimethylsilyl)amino]-1,9-dihydro-6H-purin-6-one

【CA登记号】

【分子式】C₁₂H₂₁N₅O₄Si

【分子量】327.41554

【元素组成】C 44.02% H 6.46% N 21.39% O 19.55% Si 8.58%

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：(II)

The silylation of ganciclovir (I) with TMSCl and imidazole in DMF gives the N2-silylated compound (II), which by condensation with N-benzyloxycarbonyl-L-valine-N-carboxyanhydride (III) and subsequent treatment with 3M HCl yields the monoprotected valganciclovir derivative (IV). Finally, this compound is submitted to hydrogenolysis with H2 over Pd/C in methanol/HCl.

参考文献中间体

合成目标

【1】 Sorbera, L.A.; Castañer, J.; Castañer, R.M.; Valganciclovir Hydrochloride. Drugs Fut 2000, 25, 5, 474.
【2】 Arzeno, H.B.; Beard, C.C.; Fisher, L.E.; Prince, A. (F. Hoffmann-La Roche AG); Process for preparing purine derivs.. WO 9727194 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	35312	2-amino-9-[[2-hydroxy-1-(hydroxymethyl)ethoxy]methyl]-1,9-dihydro-6H-purin-6-one		C₉H₁₃N₅O₄	详情	详情
(II)	35313	9-[[2-hydroxy-1-(hydroxymethyl)ethoxy]methyl]-2-[(trimethylsilyl)amino]-1,9-dihydro-6H-purin-6-one		C₁₂H₂₁N₅O₄Si	详情	详情
(III)	29555	benzyl (4S)-4-isopropyl-2,5-dioxo-1,3-oxazolidine-3-carboxylate	158257-41-1	C₁₄H₁₅NO₅	详情	详情
(IV)	35314	2-[(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)methoxy]-3-hydroxypropyl (2S)-2-[[(benzyloxy)carbonyl]amino]-3-methylbutanoate		C₂₂H₂₈N₆O₇	详情	详情

Extended Information