(3R)-3-{(2R,6S,9S,12R,15R,19R,22S,25R,31S,33aS,34S,39S,42R,44aS)-22-{3-[(2-cyanoethyl)amino]propyl}-2,34-dihydroxy-9-(4-hydroxybenzyl)-15,25,39,42-tetrakis[(1R)-1-hydroxyethyl]-6-isopropyl-12-methyl-5,8,11,14,17,21,24,27,30,33,38,41,44-tridecaoxo-19 -Drug Synthesis Database

【结构式】

【分子编号】58763

【品名】(3R)-3-{(2R,6S,9S,12R,15R,19R,22S,25R,31S,33aS,34S,39S,42R,44aS)-22-{3-[(2-cyanoethyl)amino]propyl}-2,34-dihydroxy-9-(4-hydroxybenzyl)-15,25,39,42-tetrakis[(1R)-1-hydroxyethyl]-6-isopropyl-12-methyl-5,8,11,14,17,21,24,27,30,33,38,41,44-tridecaoxo-19

【CA登记号】

【分子式】C₇₄H₁₁₉N₁₅O₂₃

【分子量】1586.84616

【元素组成】C 56.01% H 7.56% N 13.24% O 23.19%

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：(III)

The title compound was prepared by chemical modification of the natural macrocyclic depsipeptide RO-0093655 (I). Conjugate addition of acrylonitrile (II) to the side-chain amino group of (I) produced the aminopropionitrile derivative (III). Subsequent acylation of aminonitrile (III) with the di-Boc-protected L-ornithine (IV) gave amide (V).

参考文献中间体

合成目标

【1】 Masubuchi, K.; et al.; Synthesis and antifungal activities of novel 1,3-beta-D-glucan synthase inhibitor. Part 2. Bioorg Med Chem Lett 2001, 11, 10, 1273.
【2】 Okada, T.; et al.; Synthesis and antifungal activities of novel 1,3-beta-D-glucan synthase inhibitors. 223rd ACS Natl Meet (April 7 2002, Orlando) 2002, Abst MEDI 174.
【3】 Okada, T.; Shimma, N.; Murata, T.; Masubuchi, K.; Kohchi, M. (Basilea Pharmaceutica AG); Novel cyclic cpds.. EP 1254161; WO 0153322 .
【4】 Shimma, N.; Kobayashi, K.; Horii, I.; Yanagawa, A. (Basilea Pharmaceutica AG); Nasally administrable cyclic peptide compsns.. WO 0152894 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	50193	(3R)-3-[(2R,6S,9S,12R,15R,19R,22S,25R,31S,33aS,34S,39S,42R,44aS)-22-(3-aminopropyl)-2,34-dihydroxy-9-(4-hydroxybenzyl)-15,25,39,42-tetrakis[(1R)-1-hydroxyethyl]-6-isopropyl-12-methyl-5,8,11,14,17,21,24,27,30,33,38,41,44-tridecaoxo-19-tridecylnonatriacontahydro-1H,5H,21H-dipyrrolo[2,1-o:2,1-x][1,4,7,10,13,16,19,22,25,28,31,34,37]oxadodecaazacyclotetracontin-31-yl]-3-hydroxypropanamide		C₇₁H₁₁₆N₁₄O₂₃	详情	详情
(II)	10847	Acrylonitrile	107-13-1	C₃H₃N	详情	详情
(III)	58763	(3R)-3-{(2R,6S,9S,12R,15R,19R,22S,25R,31S,33aS,34S,39S,42R,44aS)-22-{3-[(2-cyanoethyl)amino]propyl}-2,34-dihydroxy-9-(4-hydroxybenzyl)-15,25,39,42-tetrakis[(1R)-1-hydroxyethyl]-6-isopropyl-12-methyl-5,8,11,14,17,21,24,27,30,33,38,41,44-tridecaoxo-19		C₇₄H₁₁₉N₁₅O₂₃	详情	详情
(IV)	58764	(2S)-2,5-bis[(tert-butoxycarbonyl)amino]pentanoic acid		C₁₅H₂₈N₂O₆	详情	详情
(V)	58765			C₈₉H₁₄₅N₁₇O₂₈	详情	详情

Extended Information