　 -Drug Synthesis Database

【结构式】

【分子编号】58765

【品名】　

【CA登记号】

【分子式】C₈₉H₁₄₅N₁₇O₂₈

【分子量】1901.22808

【元素组成】C 56.23% H 7.69% N 12.52% O 23.56%

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：(V)

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

合成路线2

该中间体在本合成路线中的序号：(V)

The Boc protecting groups of (V) were removed by treatment with trifluoroacetic acid yielding diamine (VI). Finally, the cyano group of (VI) was reduced by catalytic hydrogenation over Pd/C to afford the title compound.

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
(V)	58765			C₈₉H₁₄₅N₁₇O₂₈	详情	详情
(VI)	58766	(2S)-N-(3-{(2R,6S,9S,12R,15R,19R,22S,25R,31S,33aS,34S,39S,42R,44aS)-31-[(1R)-3-amino-1-hydroxy-3-oxopropyl]-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-22-yl}propyl)-2,5-diamino-N-(2-cyanoethyl)pentanamide		C₇₉H₁₂₉N₁₇O₂₄	详情	详情

Extended Information