(2S)-1-pyruvoyl-2-pyrrolidinecarboxylic acid -Drug Synthesis Database

【结构式】

【分子编号】62542

【品名】(2S)-1-pyruvoyl-2-pyrrolidinecarboxylic acid

【CA登记号】

【分子式】C₈H₁₁NO₄

【分子量】185.17968

【元素组成】C 51.89% H 5.99% N 7.56% O 34.56%

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：(XXXII)

Keto amide (XXXI) was obtained by acylation of L-proline benzyl ester (XII) with pyruvic acid (XXX). Subsequent hydrogenolysis of the benzyl ester group provided pyruvyl proline (XXXII). The target dehydrodidemnin B was then prepared by coupling of didemnin A (XXIX), from either natural or synthetic sources, with pyruvyl proline (XXXII)

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.
【2】 Rinehart, K.L.; Lithgow-Bertelloni, A.M. (PharmaMar, SA); Dehydrodidemnin B. WO 9104985 .
【3】 Giralt Lledo, E.; Albericio Palomera, F.; Lloyd-Williams, P.; Gonzalez Valcarcel, I.; Jou Prat, G.; Gomez Gonzalez, A.; Manzanares Secades, I. (PharmaMar, SA); Process for the preparation of didemnine A. ES 2102322 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(XII)	20930	benzyl (2S)-2-pyrrolidinecarboxylate	16652-71-4	C₁₂H₁₅NO₂	详情	详情
(XXIX)	50796	(2R)-N-[(3S,6R,7S,10R,11S,15S,17S,20S,25aS)-11-hydroxy-20-isobutyl-15-isopropyl-3-(4-methoxybenzyl)-2,6,17-trimethyl-10-[(1S)-1-methylpropyl]-1,4,8,13,16,18,21-heptaoxodocosahydro-15H-pyrrolo[2,1-f][1,15,4,7,10,20]dioxatetraazacyclotricosin-7-yl]-4-methyl-2-(methylamino)pentanamide		C₄₉H₇₈N₆O₁₂	详情	详情
(XXX)	24066	2-oxopropionic acid	127-17-3	C₃H₄O₃	详情	详情
(XXXI)	62541	benzyl (2S)-1-pyruvoyl-2-pyrrolidinecarboxylate		C₁₅H₁₇NO₄	详情	详情
(XXXII)	62542	(2S)-1-pyruvoyl-2-pyrrolidinecarboxylic acid		C₈H₁₁NO₄	详情	详情

合成路线2

该中间体在本合成路线中的序号：(XXXII)

N-Benzyloxycarbonyl-N-methyl-D-leucine (LX) was prepared by methylation of the N-protected D-leucine (LIX) with iodomethane in the presence of NaH. Acylation of macrocyclic amine (XXV) with the N-protected aminoacid (LX) furnished the N-carbobenzoxy didemnin A (LXI). The title compound was then obtained by hydrogenolysis of the N-carbobenzoxy group of (LXI), followed by acylation with pyruvyl proline (XXXII) by means of diisopropyl carbodiimide

参考文献中间体

合成目标

【1】 Edge, A. (Diacrin, Inc.); Method for improving graft acceptance in a recipient by administration of a cytokine profile altering agent. WO 0051630 .

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(XXV)	50768	(3S,6R,7S,10R,11S,15S,17S,20S,25aS)-7-amino-11-hydroxy-20-isobutyl-15-isopropyl-3-(4-methoxybenzyl)-2,6,17-trimethyl-10-[(1S)-1-methylpropyl]tetradecahydro-15H-pyrrolo[2,1-f][1,15,4,7,10,20]dioxatetraazacyclotricosine-1,4,8,13,16,18,21(17H)-heptone	C₄₂H₆₅N₅O₁₁	详情	详情
(XXXII)	62542	(2S)-1-pyruvoyl-2-pyrrolidinecarboxylic acid	C₈H₁₁NO₄	详情	详情
(LIX)	22838	(2S)-2-[[(benzyloxy)carbonyl]amino]-4-methylpentanoic acid	C₁₄H₁₉NO₄	详情	详情
(LXI)	50810	benzyl (1R)-1-[([(3S,6R,7S,10R,11S,15S,17S,20S,25aS)-11-hydroxy-20-isobutyl-15-isopropyl-3-(4-methoxybenzyl)-2,6,17-trimethyl-10-[(1S)-1-methylpropyl]-1,4,8,13,16,18,21-heptaoxodocosahydro-15H-pyrrolo[2,1-f][1,15,4,7,10,20]dioxatetraazacyclotricosin	C₅₇H₈₄N₆O₁₄	详情	详情

Extended Information