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【结 构 式】 
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【分子编号】15475 【品名】(3S,6S,9S,12R,15S,18S,21S,24S,30S,33S)-33-[(1R,2R,4E)-1-hydroxy-2-methyl-4-hexenyl]-6,9,18,24-tetraisobutyl-3,21,30-triisopropyl-1,4,7,10,12,15,19,25,28-nonamethyl-1,4,7,10,13,16,19,22,25,28,31-undecaazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29,32-undecone 【CA登记号】 |
【 分 子 式 】C63H113N11O12 【 分 子 量 】1216.65716 【元素组成】C 62.19% H 9.36% N 12.66% O 15.78% |
合成路线1
该中间体在本合成路线中的序号：(I)By oxidation of cyclosporin D (I) with N-chlorosuccinimide (II) and dimethylsulfide in toluene.
| 【1】 Robinson, C.; Castaner, J.; PSC-833. Drugs Fut 1995, 20, 10, 1010. |
| 【2】 Bollinger, P.; Bolsterli, J.J.; Borel, J.-F.; Krieger, M.; Payne, T.G.; Traber, R.P.; Wenger, R. (Novartis AG); Cyclosporins and their use as pharmaceuticals. AU 8817679; EP 0296122; JP 1989045396; JP 1996048696; US 5525590 . |
| 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) | 15475 | (3S,6S,9S,12R,15S,18S,21S,24S,30S,33S)-33-[(1R,2R,4E)-1-hydroxy-2-methyl-4-hexenyl]-6,9,18,24-tetraisobutyl-3,21,30-triisopropyl-1,4,7,10,12,15,19,25,28-nonamethyl-1,4,7,10,13,16,19,22,25,28,31-undecaazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29,32-undecone | C63H113N11O12 | 详情 | 详情 | |
| (II) | 40429 | Succinchlorimide; N-Chlorosuccinimide; 1-chloro-2,5-pyrrolidinedione | 128-09-6 | C4H4ClNO2 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(XI)The reaction of (IX) first with NaOH in ethanol to hydrolyze the terminal ester group, and then with TFA to eliminate the terminal tert-butoxycarbonyl group gives the fully deprotected peptide (X), which is cyclized by means of BOP and NMM in dichloromethane yielding the cyclic peptide (XI). Finally, this compound is oxidized by the modified Pfitzer-Moffat method with DMSO and DCC in tert-butyl methyl ether.
| 【1】 Metz, Y.; Kohler, B.; Burtscher, P.; Voges, R.; Wenger, R.; Synthesis of [S-[1-C-14]Val(7)]VALSPODAR application of (+)/(-)-[C-13,14(N)]BABS and (+)/(-)-[C-13,14(N)]DPMGBS, part 4. J Label Compd Radiopharm 2000, 43, 3, 205. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (IX) | 41054 | C69H125N11O15 | 详情 | 详情 | ||
| (X) | 41055 | C63H115N11O13 | 详情 | 详情 | ||
| (XI) | 15475 | (3S,6S,9S,12R,15S,18S,21S,24S,30S,33S)-33-[(1R,2R,4E)-1-hydroxy-2-methyl-4-hexenyl]-6,9,18,24-tetraisobutyl-3,21,30-triisopropyl-1,4,7,10,12,15,19,25,28-nonamethyl-1,4,7,10,13,16,19,22,25,28,31-undecaazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29,32-undecone | C63H113N11O12 | 详情 | 详情 |