N-(9-[[2-hydroxy-1-(hydroxymethyl)ethoxy]methyl]-6-oxo-6,9-dihydro-1H-purin-2-yl)acetamide -Drug Synthesis Database

【结构式】

【分子编号】46048

【品名】N-(9-[[2-hydroxy-1-(hydroxymethyl)ethoxy]methyl]-6-oxo-6,9-dihydro-1H-purin-2-yl)acetamide

【CA登记号】

【分子式】C₁₁H₁₅N₅O₅

【分子量】297.2708

【元素组成】C 44.44% H 5.09% N 23.56% O 26.91%

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：(VII)

The reaction of 1,3-dichloro-2-propanol (I) with Bn-ONa gives 1,3-dibenzyloxy-2-propanol (II), which by reaction with paraformaldehyde and HCl is converted into the chloromethyl ether (III). The reaction of (III) with potassium acetate affords the acetoxymethyl ether (IV), which is condensed with diacetylguanine (V) by means of TsOH to provide fully protected ganciclovir (VI). Finally, this compound is debenzylated to (VII) with Pd(OH)2/cyclohexene and deacetylated with ammonia in methanol.

参考文献中间体

合成目标

【1】 Gao, H.; Mitra, A.K.; Synthesis of acyclovir, ganciclovir and their prodrugs: A review. Synthesis 2000, 3, 329.

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)	33378	1,3-dichloro-2-propanol	96-23-1	C₃H₆Cl₂O	详情	详情
(II)	29159	1,3-bis(benzyloxy)-2-propanol	6972-79-8	C₁₇H₂₀O₃	详情	详情
(III)	24432	1-[[3-(benzyloxy)-2-(chloromethoxy)propoxy]methyl]benzene		C₁₈H₂₁ClO₃	详情	详情
(IV)	29160	[2-(benzyloxy)-1-[(benzyloxy)methyl]ethoxy]methyl acetate		C₂₀H₂₄O₅	详情	详情
(V)	29161	N-(9-acetyl-6-oxo-6,9-dihydro-1H-purin-2-yl)acetamide; N2,9-Diacetylguanine	3056-33-5	C₉H₉N₅O₃	详情	详情
(VI)	29162	N-[9-([2-(benzyloxy)-1-[(benzyloxy)methyl]ethoxy]methyl)-6-oxo-6,9-dihydro-1H-purin-2-yl]acetamide		C₂₅H₂₇N₅O₅	详情	详情
(VII)	46048	N-(9-[[2-hydroxy-1-(hydroxymethyl)ethoxy]methyl]-6-oxo-6,9-dihydro-1H-purin-2-yl)acetamide		C₁₁H₁₅N₅O₅	详情	详情

Extended Information