methyl (9S,12S)-4-methoxy-12-[[(2S,5S,8S,11R)-5-(4-methoxybenzyl)-2,6,8,11,15,15-hexamethyl-4,7,10,13-tetraoxo-14-oxa-3,6,9,12-tetraazahexadec-1-anoyl](methyl)amino]-11-oxo-2-oxa-10-azatricyclo[12.2.2.1(3,7)]nonadeca-1(16),3(19),4,6,14,17-hexaene-9-carboxylate -Drug Synthesis Database

【结构式】

【分子编号】26449

【品名】methyl (9S,12S)-4-methoxy-12-[[(2S,5S,8S,11R)-5-(4-methoxybenzyl)-2,6,8,11,15,15-hexamethyl-4,7,10,13-tetraoxo-14-oxa-3,6,9,12-tetraazahexadec-1-anoyl](methyl)amino]-11-oxo-2-oxa-10-azatricyclo[12.2.2.1(3,7)]nonadeca-1(16),3(19),4,6,14,17-hexaene-9-carboxylate

【CA登记号】

【分子式】C₄₆H₆₀N₆O₁₂

【分子量】889.01564

【元素组成】C 62.15% H 6.8% N 9.45% O 21.6%

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：(XVII)

The condensation of (XIII) with N-protected L-alanine (XIV) by means of PyBrOP and diethylisopropylamine in DMF gives the cyclic tripeptide (XV), which after deprotection with TFA is condensed with the protected tripeptide (XVI) by means of EDC and HOBT to provide the cyclic hexapeptide (XVII). Finally, this compound is cyclized by hydrolysis of the methyl ester with LiOH in THF/methanol/water, deprotection of the amino group with TFA and cyclization with DPPA and NaHCO3 in DMF.

参考文献中间体

合成目标

【1】 Bigot, A.; et al.; Total synthesis of an antitumor agent RA-VII via an efficient preparation of cycloisodityrosine. J Org Chem 1999, 64, 17, 6283.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(XIII)	26446	methyl (9S,12S)-4-methoxy-12-(methylamino)-11-oxo-2-oxa-10-azatricyclo[12.2.2.1(3,7)]nonadeca-1(16),3(19),4,6,14,17-hexaene-9-carboxylate		C₂₁H₂₄N₂O₅	详情	详情
(XIV)	26450	Boc-L-Alanine;(S)-2-((tert-butoxycarbonyl)amino)propanoic acid;N-Boc-L-alanine; (2S)-2-[(tert-butoxycarbonyl)amino]propionic acid	15761-38-3	C₈H₁₅NO₄	详情	详情
(XV)	26447	methyl (9S,12S)-12-[[(2S)-2-[(tert-butoxycarbonyl)amino]propanoyl](methyl)amino]-4-methoxy-11-oxo-2-oxa-10-azatricyclo[12.2.2.1(3,7)]nonadeca-1(16),3(19),4,6,14,17-hexaene-9-carboxylate		C₂₉H₃₇N₃O₈	详情	详情
(XVI)	26448	(6R,9S,12S)-12-(4-methoxybenzyl)-2,2,6,9,11-pentamethyl-4,7,10-trioxo-3-oxa-5,8,11-triazatridecan-13-oic acid		C₂₂H₃₃N₃O₇	详情	详情
(XVII)	26449	methyl (9S,12S)-4-methoxy-12-[[(2S,5S,8S,11R)-5-(4-methoxybenzyl)-2,6,8,11,15,15-hexamethyl-4,7,10,13-tetraoxo-14-oxa-3,6,9,12-tetraazahexadec-1-anoyl](methyl)amino]-11-oxo-2-oxa-10-azatricyclo[12.2.2.1(3,7)]nonadeca-1(16),3(19),4,6,14,17-hexaene-9-carboxylate		C₄₆H₆₀N₆O₁₂	详情	详情

Extended Information