methyl (Z)-2-bromo-5-[(tert-butoxycarbonyl)(5-[[tert-butyl(diphenyl)silyl]oxy]pentyl)amino]-2-pentenoate -Drug Synthesis Database

【结构式】

【分子编号】24914

【品名】methyl (Z)-2-bromo-5-[(tert-butoxycarbonyl)(5-[[tert-butyl(diphenyl)silyl]oxy]pentyl)amino]-2-pentenoate

【CA登记号】

【分子式】C₃₂H₄₆BrNO₅Si

【分子量】632.71048

【元素组成】C 60.75% H 7.33% Br 12.63% N 2.21% O 12.64% Si 4.44%

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)

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