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【结 构 式】 
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【分子编号】47007 【品名】N-[(2R,6S,9S,11R,12S,14aS,15S,20S,23S,25aS)-12-[(2-aminoethyl)sulfanyl]-20-[(1R)-3-amino-1-hydroxypropyl]-23-[(1S,2S)-1,2-dihydroxy-2-(4-hydroxyphenyl)ethyl]-2,11,15-trihydroxy-6-[(1R)-1-hydroxyethyl]-5,8,14,19,22,25-hexaoxotetracosahydro-1H-dipyrrolo[2,1-c:2,1-l][1,4,7,10,13,16]hexaazacyclohenicosin-9-yl]-10,12-dimethyltetradecanamide 【CA登记号】 |
【 分 子 式 】C52H87N9O15S 【 分 子 量 】1110.38044 【元素组成】C 56.25% H 7.9% N 11.35% O 21.61% S 2.89% |
合成路线1
该中间体在本合成路线中的序号：(IV)
| 【1】 Bouffard FA.Zambias RA,Dropinski.JF,et aL 1994.Synthesis and antifungal activity of novel cationic poeumocandin B derivatives J Med Chem, 37: 222～225 |
| 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) | 47003 | N-[(2R,6S,9S,11R,12R,14aS,15S,20S,23S,25aS)-20-[(1R)-3-amino-1-hydroxy-3-oxopropyl]-23-[(1S,2S)-1,2-dihydroxy-2-(4-hydroxyphenyl)ethyl]-2,11,12,15-tetrahydroxy-6-[(1R)-1-hydroxyethyl]-5,8,14,19,22,25-hexaoxotetracosahydro-1H-dipyrrolo[2,1-c:2,1-l][1,4,7,10,13,16]hexaazacyclohenicosin-9-yl]-10,12-dimethyltetradecanamide | C50H80N8O17 | 详情 | 详情 | |
| (II) | 66161 | C50H80N8O15 | 详情 | 详情 | ||
| (III) | 47005 | N-[(2R,6S,9S,11R,12R,14aS,15S,20S,23S,25aS)-20-[(1R)-3-amino-1-hydroxypropyl]-23-[(1S)-1,2-dihydroxy-2-(4-hydroxyphenyl)ethyl]-2,11,12,15-tetrahydroxy-6-[(1R)-1-hydroxyethyl]-5,8,14,19,22,25-hexaoxotetracosahydro-1H-dipyrrolo[2,1-c:2,1-l][1,4,7,10,13,16]hexaazacyclohenicosin-9-yl]-10,12-dimethyltetradecanamide | C50H82N8O16 | 详情 | 详情 | |
| (IV) | 47007 | N-[(2R,6S,9S,11R,12S,14aS,15S,20S,23S,25aS)-12-[(2-aminoethyl)sulfanyl]-20-[(1R)-3-amino-1-hydroxypropyl]-23-[(1S,2S)-1,2-dihydroxy-2-(4-hydroxyphenyl)ethyl]-2,11,15-trihydroxy-6-[(1R)-1-hydroxyethyl]-5,8,14,19,22,25-hexaoxotetracosahydro-1H-dipyrrolo[2,1-c:2,1-l][1,4,7,10,13,16]hexaazacyclohenicosin-9-yl]-10,12-dimethyltetradecanamide | C52H87N9O15S | 详情 | 详情 | |
| (V) | 66162 | C52H87N9O15S | 详情 | 详情 | ||
| (VI) | 66163 | C56H84N8O16S | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(VII)The reaction of cyclopeptide (V) with 2-sulfanylethylamine (VI) by means of camphorsulfonic acid (CSA) in DMF gives the epi-2-aminoethylsulfanyl compound (VII), which is oxidized with oxone in acetonitrile/water, affording the sulfone (VIII). Finally, this compound is treated with ethylenediamine in DMF to afford the target compound.
| 【1】 Balkovec, J.M.; Bouffard, F.A.; Black, R.M. (Merck & Co., Inc.); Aza cyclohexapeptide cpds.. CA 2118757; EP 0620232; JP 1994321986; US 5378804; WO 9421677 . |
| 【2】 Balkovec, J.M.; Black, R.M.; Bouffard, F.A. (Merck & Co., Inc.); Aza cyclohexapeptide cpds.. US 5792746 . |
| 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) | 47005 | N-[(2R,6S,9S,11R,12R,14aS,15S,20S,23S,25aS)-20-[(1R)-3-amino-1-hydroxypropyl]-23-[(1S)-1,2-dihydroxy-2-(4-hydroxyphenyl)ethyl]-2,11,12,15-tetrahydroxy-6-[(1R)-1-hydroxyethyl]-5,8,14,19,22,25-hexaoxotetracosahydro-1H-dipyrrolo[2,1-c:2,1-l][1,4,7,10,13,16]hexaazacyclohenicosin-9-yl]-10,12-dimethyltetradecanamide | C50H82N8O16 | 详情 | 详情 | |
| (VI) | 13186 | 2-Aminoethanethiol; 2-Amino-1-ethanethiol; 2-Aminoethylhydrosulfide; Cysteamine | 60-23-1 | C2H7NS | 详情 | 详情 |
| (VII) | 47007 | N-[(2R,6S,9S,11R,12S,14aS,15S,20S,23S,25aS)-12-[(2-aminoethyl)sulfanyl]-20-[(1R)-3-amino-1-hydroxypropyl]-23-[(1S,2S)-1,2-dihydroxy-2-(4-hydroxyphenyl)ethyl]-2,11,15-trihydroxy-6-[(1R)-1-hydroxyethyl]-5,8,14,19,22,25-hexaoxotetracosahydro-1H-dipyrrolo[2,1-c:2,1-l][1,4,7,10,13,16]hexaazacyclohenicosin-9-yl]-10,12-dimethyltetradecanamide | C52H87N9O15S | 详情 | 详情 | |
| (VIII) | 47008 | N-[(2R,6S,9S,11R,12S,14aS,15S,20S,23S,25aS)-12-[(2-aminoethyl)sulfonyl]-20-[(1R)-3-amino-1-hydroxypropyl]-23-[(1S,2S)-1,2-dihydroxy-2-(4-hydroxyphenyl)ethyl]-2,11,15-trihydroxy-6-[(1R)-1-hydroxyethyl]-5,8,14,19,22,25-hexaoxotetracosahydro-1H-dipyrrolo[2,1-c:2,1-l][1,4,7,10,13,16]hexaazacyclohenicosin-9-yl]-10,12-dimethyltetradecanamide | C52H87N9O17S | 详情 | 详情 |