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【结 构 式】 
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【分子编号】31380 【品名】S-[(2S,5S,8R,11S,14S,17R)-17-([[(1S)-2-amino-1-(2-naphthylmethyl)-2-oxoethyl]amino]carbonyl)-2-[[(2S)-2-[(tert-butoxycarbonyl)amino]-3-(4-chlorophenyl)propanoyl]amino]-14-(tert-butyl)-11-[4-([[(2-chlorobenzyl)oxy]carbonyl]amino)butyl]-8-(1H-indol-3- 【CA登记号】 |
【 分 子 式 】C90H102Cl2N12O16S2 【 分 子 量 】1742.90856 【元素组成】C 62.02% H 5.9% Cl 4.07% N 9.64% O 14.69% S 3.68% |
合成路线1
该中间体在本合成路线中的序号：(XVIII)Compound (XIV) was subsequently submitted to further coupling and deprotection cycles with the protected amino acids N-Boc-S-(4-methylbenzyloxycarbonyl)-D-cysteine (XV) and N-Boc-L-(4-chlorophenyl)- alanine (XVII) to afford the peptide-resins (XVI) and (XVIII), respectively.
| 【1】 Taylor, J.E.; Hocart, S.J.; Murphy, W.A.; Coy, D.H.; Jian, R.; Highly potent cyclic disulfide antagonists of somatostatin. J Med Chem 1999, 42, 11, 1863. |
| 【2】 Murphy, W.; Coy, D.H.; Morgan, B. (Biomeasure Inc.; Tulane Educational Fund); Somatostatin antagonists. WO 9824807 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XIV) | 31376 | S-[(2R,5S,8S)-2-([[(1S)-2-amino-1-(2-naphthylmethyl)-2-oxoethyl]amino]carbonyl)-8-[[(2R)-2-[[(2S)-2-amino-3-(3-pyridinyl)propanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-5-(tert-butyl)-16-(2-chlorophenyl)-4,7,14-trioxo-15-oxa-3,6,13-triazahexadec- | C64H73ClN10O10S | 详情 | 详情 | |
| (XV) | 31382 | (2S)-2-[(tert-butoxycarbonyl)amino]-3-([[(4-methylbenzyl)oxy]carbonyl]sulfanyl)propionic acid | C17H23NO6S | 详情 | 详情 | |
| (XVI) | 31379 | S-[(2R,5S,8S,11R,14S,17S)-17-amino-2-([[(1S)-2-amino-1-(2-naphthylmethyl)-2-oxoethyl]amino]carbonyl)-5-(tert-butyl)-8-[4-([[(2-chlorobenzyl)oxy]carbonyl]amino)butyl]-11-(1H-indol-3-ylmethyl)-22-(4-methylphenyl)-4,7,10,13,16,20-hexaoxo-14-(3-pyridiny | C76H86ClN11O13S2 | 详情 | 详情 | |
| (XVII) | 31381 | (2S)-2-[(tert-butoxycarbonyl)amino]-3-(4-chlorophenyl)propionic acid | 68090-88-0 | C14H18ClNO4 | 详情 | 详情 |
| (XVIII) | 31380 | S-[(2S,5S,8R,11S,14S,17R)-17-([[(1S)-2-amino-1-(2-naphthylmethyl)-2-oxoethyl]amino]carbonyl)-2-[[(2S)-2-[(tert-butoxycarbonyl)amino]-3-(4-chlorophenyl)propanoyl]amino]-14-(tert-butyl)-11-[4-([[(2-chlorobenzyl)oxy]carbonyl]amino)butyl]-8-(1H-indol-3- | C90H102Cl2N12O16S2 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(XVIII)Cleavage of the peptide (XVIII) from the resin support with simultaneous side-chain deprotection using anhydrous HF containing the scavengers anisole and dithiothreitol produced the peptide amide (XIX). This was finally cyclized to the title disulfide employing iodine in AcOH.
| 【1】 Taylor, J.E.; Hocart, S.J.; Murphy, W.A.; Coy, D.H.; Jian, R.; Highly potent cyclic disulfide antagonists of somatostatin. J Med Chem 1999, 42, 11, 1863. |
| 【2】 Murphy, W.; Coy, D.H.; Morgan, B. (Biomeasure Inc.; Tulane Educational Fund); Somatostatin antagonists. WO 9824807 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XVIII) | 31380 | S-[(2S,5S,8R,11S,14S,17R)-17-([[(1S)-2-amino-1-(2-naphthylmethyl)-2-oxoethyl]amino]carbonyl)-2-[[(2S)-2-[(tert-butoxycarbonyl)amino]-3-(4-chlorophenyl)propanoyl]amino]-14-(tert-butyl)-11-[4-([[(2-chlorobenzyl)oxy]carbonyl]amino)butyl]-8-(1H-indol-3- | C90H102Cl2N12O16S2 | 详情 | 详情 | |
| (XIX) | 31383 | (2S,5R,8S,11S,14R,17S,20S,23S)-23-amino-11-(4-aminobutyl)-8-(tert-butyl)-24-(4-chlorophenyl)-14-(1H-indol-3-ylmethyl)-2-(2-naphthylmethyl)-4,7,10,13,16,19,22-heptaoxo-17-(3-pyridinylmethyl)-5,20-bis(sulfanylmethyl)-3,6,9,12,15,18,21-heptaazatetracos | C59H73ClN12O8S2 | 详情 | 详情 |