5-amino-1-pentanol -Drug Synthesis Database

【结构式】

【分子编号】22846

【品名】5-amino-1-pentanol

【CA登记号】2508-29-4

【分子式】C₅H₁₃NO

【分子量】103.16436

【元素组成】C 58.21% H 12.7% N 13.58% O 15.51%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(II)

The reaction of 4,6-dichloropyrimidin-5-amine (I) with 5-aminopentanol (I) gives 4-chloro-6-(5-hydroxypentylamino)pyrimidin-5 amine (III), which is cyclized with triethyl orthoformate (IV) yielding 6-chloro-9-(5-hydroxypentyl)purine (V). The hydrolysis of (V) with formic acid affords 9-(5-hydroxypentyl) hypoxanthine (VI), which is treated with phosgene (VII) to give 9-[5-(chlorocarbonyloxy)pentyl]hypoxanthine (VIII). Finally, this compound is condensed with arginine (IX).

参考文献中间体

合成目标

【1】 Stradi, R.; Cornaglia-Ferraris, P.; Perezzani, L.S.; Forni, G.; Riccardi, C.; PCF-39. Drugs Fut 1987, 12, 2, 134.

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)	22845	5-Amino-4,6-dichloropyrimidine; 4,6-dichloro-5-pyrimidinylamine; 4,6-dichloro-5-pyrimidinamine	5413-85-4	C₄H₃Cl₂N₃	详情	详情
(II)	22846	5-amino-1-pentanol	2508-29-4	C₅H₁₃NO	详情	详情
(III)	22847	5-[(5-amino-6-chloro-4-pyrimidinyl)amino]-1-pentanol		C₉H₁₅ClN₄O	详情	详情
(IV)	21304	Triethyl orthoformate; 1-(Diethoxymethoxy)ethane; Diethoxymethyl ethyl ether	122-51-0	C₇H₁₆O₃	详情	详情
(V)	22849	5-(6-chloro-9H-purin-9-yl)-1-pentanol		C₁₀H₁₃ClN₄O	详情	详情
(VI)	22850	9-(5-hydroxypentyl)-9H-purin-6-ol		C₁₀H₁₄N₄O₂	详情	详情
(VIII)	22852	9-[5-[(chlorocarbonyl)oxy]pentyl]-6-hydroxy-9H-purine		C₁₁H₁₃ClN₄O₃	详情	详情
(IX)	22853	Arginine; 2-Amino-5-guanidinopentanoic acid		C₆H₁₄N₄O₂	详情	详情

合成路线2

该中间体在本合成路线中的序号：(I)

The protection of 5-amino-1-pentanol (I) gives the fully protected compound (II), which is condensed with propenal (III) yielding the 3-aminopropanal derivative (IV). The condensation of aldehyde (IV) with phosphorane (V) yielded the protected 5-amino-2-bromopentenoic ester derivative (VI), which is deprotected with trimethylsilyl triflate to afford the ester (VII) with an unprotected secondary amino group.

参考文献中间体

合成目标

【1】 Martin, S.F.; et al.; Enantioselective total synthesis of ircinal A and related manzamine alkaloids. J Am Chem Soc 1999, 121, 4, 866.

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)	22846	5-amino-1-pentanol	2508-29-4	C₅H₁₃NO	详情	详情
(II)	24910	tert-butyl 5-[[tert-butyl(diphenyl)silyl]oxy]pentylcarbamate		C₂₆H₃₉NO₃Si	详情	详情
(III)	17668	acrylaldehyde; Acrolein	107-02-8	C₃H₄O	详情	详情
(IV)	24912	tert-butyl 5-[[tert-butyl(diphenyl)silyl]oxy]pentyl(3-oxopropyl)carbamate		C₂₉H₄₃NO₄Si	详情	详情
(V)	24913	methyl 2-bromo-2-(triphenylphosphoranylidene)acetate		C₂₁H₁₈BrO₂P	详情	详情
(VI)	24914	methyl (Z)-2-bromo-5-[(tert-butoxycarbonyl)(5-[[tert-butyl(diphenyl)silyl]oxy]pentyl)amino]-2-pentenoate		C₃₂H₄₆BrNO₅Si	详情	详情
(VII)	24915	methyl (Z)-2-bromo-5-[(5-[[tert-butyl(diphenyl)silyl]oxy]pentyl)amino]-2-pentenoate		C₂₇H₃₈BrNO₃Si	详情	详情

Extended Information