(2S)-1-{(2S,7S,11S,12R,15S,16R,19S)-15-({(2R)-2-[(tert-butoxycarbonyl)(methyl)amino]-4-methylpentanoyl}amino)-11-{[tert-butyl(dimethyl)silyl]oxy}-2-isobutyl-7-isopropyl-19-(4-methoxybenzyl)-5,16,20-trimethyl-12-[(1S)-1-methylpropyl]-4,6,9,14,18,21-h -Drug Synthesis Database

【结构式】

【分子编号】62558

【品名】(2S)-1-{(2S,7S,11S,12R,15S,16R,19S)-15-({(2R)-2-[(tert-butoxycarbonyl)(methyl)amino]-4-methylpentanoyl}amino)-11-{[tert-butyl(dimethyl)silyl]oxy}-2-isobutyl-7-isopropyl-19-(4-methoxybenzyl)-5,16,20-trimethyl-12-[(1S)-1-methylpropyl]-4,6,9,14,18,21-h

【CA登记号】

【分子式】C₆₈H₁₀₈N₆O₁₇Si

【分子量】1309.72126

【元素组成】C 62.36% H 8.31% N 6.42% O 20.77% Si 2.14%

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：(LII)

Sequential deprotection of the trichloroethyl ester and the N-benzyloxycarbonyl groups of (LI) led to (LII) and the linear aminoacid (LIII), which underwent macrocyclization to the N-Boc didemnin A (XXVIII) upon treatment with HATU and HOAt. The title compound was then obtained by acidic Boc group deprotection, followed by coupling with pyruvyl proline as outlined in Schemes 23437701e and 23437701f

参考文献中间体

合成目标

【1】 Jou, G.; Gonzalez, I.; Albericio, F.; Lloyd-Williams, P.; Giralt, E.; Total synthesis of dehydrodidemnin B. Use of uronium and phosphonium salt coupling reagents in peptide synthesis in solution. J Org Chem 1997, 62, 2, 354.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(XXVIII)	62560		C₆₀H₁₀₀N₆O₁₄Si	详情	详情
(LI)	62557	2,2,2-trichloroethyl (2S)-1-{(2S,7S,11S,12R,15S,16R,19S)-15-({(2R)-2-[(tert-butoxycarbonyl)(methyl)amino]-4-methylpentanoyl}amino)-11-{[tert-butyl(dimethyl)silyl]oxy}-2-isobutyl-7-isopropyl-19-(4-methoxybenzyl)-5,16,20-trimethyl-12-[(1S)-1-methylpro	C₇₀H₁₀₉Cl₃N₆O₁₇Si	详情	详情
(LII)	62558	(2S)-1-{(2S,7S,11S,12R,15S,16R,19S)-15-({(2R)-2-[(tert-butoxycarbonyl)(methyl)amino]-4-methylpentanoyl}amino)-11-{[tert-butyl(dimethyl)silyl]oxy}-2-isobutyl-7-isopropyl-19-(4-methoxybenzyl)-5,16,20-trimethyl-12-[(1S)-1-methylpropyl]-4,6,9,14,18,21-h	C₆₈H₁₀₈N₆O₁₇Si	详情	详情
(LIII)	62559	(2S)-1-{(2S,7S,11S,12R,15S,18R)-11-{[tert-butyl(dimethyl)silyl]oxy}-2,18-diisobutyl-7-isopropyl-15-((1R)-1-{[(2S)-3-(4-methoxyphenyl)-2-(methylamino)propanoyl]oxy}ethyl)-5,19,22,22-tetramethyl-12-[(1S)-1-methylpropyl]-4,6,9,14,17,20-hexaoxo-8,21-dio	C₆₀H₁₀₂N₆O₁₅Si	详情	详情

Extended Information