benzyl (2S)-1-pyruvoyl-2-pyrrolidinecarboxylate -Drug Synthesis Database

【结构式】

【分子编号】62541

【品名】benzyl (2S)-1-pyruvoyl-2-pyrrolidinecarboxylate

【CA登记号】

【分子式】C₁₅H₁₇NO₄

【分子量】275.30432

【元素组成】C 65.44% H 6.22% N 5.09% O 23.25%

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：(XXXI)

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

Extended Information