2,2,2-trichloroethyl (2S)-1-((2S)-2-{[(4S)-4-hydroxy-2,5-dimethyl-3-oxohexanoyl]amino}-4-methylpentanoyl)-2-pyrrolidinecarboxylate -Drug Synthesis Database

【结构式】

【分子编号】62549

【品名】2,2,2-trichloroethyl (2S)-1-((2S)-2-{[(4S)-4-hydroxy-2,5-dimethyl-3-oxohexanoyl]amino}-4-methylpentanoyl)-2-pyrrolidinecarboxylate

【CA登记号】

【分子式】C₂₁H₃₃Cl₃N₂O₆

【分子量】515.861

【元素组成】C 48.9% H 6.45% Cl 20.62% N 5.43% O 18.61%

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：(XL)

In an alternative synthesis, the previously reported trichloroethyl ester (XXXVI) was deprotected by treatment with zinc dust in the presence of ammonium acetate yielding acid (XXXVII). This was then coupled to proline trichloroethyl ester (XXXVIII), prepared from N-Boc-L-proline (XXXIII), to furnish amide (XXXIX). Subsequent hydrogenolysis of the O-benzyl group of (XXXIX) provided intermediate (XL)

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
(XXXIII)	16734	(2S)-1-(tert-butoxycarbonyl)tetrahydro-1H-pyrrole-2-carboxylic acid; N-alpha-t-BOC-L-proline; (2S)-1-(tert-butoxycarbonyl)-2-pyrrolidinecarboxylic acid	C₁₀H₁₇NO₄	详情	详情
(XXXVI)	62545	2,2,2-trichloroethyl (2S)-2-{[(4S)-4-(benzyloxy)-2,5-dimethyl-3-oxohexanoyl]amino}-4-methylpentanoate	C₂₃H₃₂Cl₃NO₅	详情	详情
(XXXVII)	62546	(2S)-2-{[(4S)-4-(benzyloxy)-2,5-dimethyl-3-oxohexanoyl]amino}-4-methylpentanoic acid	C₂₁H₃₁NO₅	详情	详情
(XXXVIII)	62547	2,2,2-trichloroethyl (2S)-2-pyrrolidinecarboxylate	C₇H₁₀Cl₃NO₂	详情	详情
(XXXIX)	62548	2,2,2-trichloroethyl (2S)-1-((2S)-2-{[(4S)-4-(benzyloxy)-2,5-dimethyl-3-oxohexanoyl]amino}-4-methylpentanoyl)-2-pyrrolidinecarboxylate	C₂₈H₃₉Cl₃N₂O₆	详情	详情
(XL)	62549	2,2,2-trichloroethyl (2S)-1-((2S)-2-{[(4S)-4-hydroxy-2,5-dimethyl-3-oxohexanoyl]amino}-4-methylpentanoyl)-2-pyrrolidinecarboxylate	C₂₁H₃₃Cl₃N₂O₆	详情	详情

合成路线2

该中间体在本合成路线中的序号：(XL)

Esterification of the peptide alcohol (XLVIII) with the modified tyrosine derivative (II) afforded depsipeptide (XLIX). After reductive cleavage of the trichloroethyl ester of (XLIX), using zinc dust and ammonium acetate, the resultant carboxylic acid (L) was coupled to the alcohol segment (XL) in the presence of DIC and DMAP·CF3COOH to furnish the linear precursor depsipeptide (LI)

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
(II)	50747	(2S)-2-[[(benzyloxy)carbonyl](methyl)amino]-3-(4-methoxyphenyl)propionic acid	C₁₉H₂₁NO₅	详情	详情
(XL)	62549	2,2,2-trichloroethyl (2S)-1-((2S)-2-{[(4S)-4-hydroxy-2,5-dimethyl-3-oxohexanoyl]amino}-4-methylpentanoyl)-2-pyrrolidinecarboxylate	C₂₁H₃₃Cl₃N₂O₆	详情	详情
(XLVIII)	50784	2,2,2-trichloroethyl (6R,9S,12R,13S)-13-[[tert-butyl(dimethyl)silyl]oxy]-9-[(1R)-1-hydroxyethyl]-6-isobutyl-2,2,5-trimethyl-12-[(1S)-1-methylpropyl]-4,7,10-trioxo-3-oxa-5,8,11-triazapentadecan-15-oate	C₃₂H₆₀Cl₃N₃O₈Si	详情	详情
(XLIX)	62555	2,2,2-trichloroethyl (5S,8R,9S,12R,13S)-9-({(2R)-2-[(tert-butoxycarbonyl)(methyl)amino]-4-methylpentanoyl}amino)-13-{[tert-butyl(dimethyl)silyl]oxy}-5-(4-methoxybenzyl)-4,8-dimethyl-12-[(1S)-1-methylpropyl]-3,6,10-trioxo-1-phenyl-2,7-dioxa-4,11-diaz	C₅₁H₇₉Cl₃N₄O₁₂Si	详情	详情
(L)	62556	(5S,8R,9S,12R,13S)-9-({(2R)-2-[(tert-butoxycarbonyl)(methyl)amino]-4-methylpentanoyl}amino)-13-{[tert-butyl(dimethyl)silyl]oxy}-5-(4-methoxybenzyl)-4,8-dimethyl-12-[(1S)-1-methylpropyl]-3,6,10-trioxo-1-phenyl-2,7-dioxa-4,11-diazapentadecan-15-oic ac	C₄₉H₇₈N₄O₁₂Si	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

Extended Information