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【结 构 式】 
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【分子编号】29886 【品名】(3S,9S,12R,16S)-6-[(Z)ethylidene]-3,12-diisopropyl-16-[(E)-4-(tritylsulfanyl)-1-butenyl]-9-[(tritylsulfanyl)methyl]-1-oxa-4,7,10,13-tetraazacyclohexadecane-2,5,8,11,14-pentone 【CA登记号】 |
【 分 子 式 】C62H66N4O6S2 【 分 子 量 】1027.3614 【元素组成】C 72.48% H 6.48% N 5.45% O 9.34% S 6.24% |
合成路线1
该中间体在本合成路线中的序号：(X)(iii) An intramolecular oxidative coupling of the thiols to form a 15-membered disulfide-containing ring: To complete the synthesis of FR901228, the beta-hydroxymercaptoheptenoic acid (VIII) was coupled to the 16-membered cyclic depsipeptide (IV) using the BOP reagent, followed by LiOH-mediated hydrolysis, resulting in the free acid product (IX). Cyclization of the hydroxy acid (IX) with TsOH, DEAD and PPh3 and oxidation of the bis(S-triphenylmethyl)lactone (X) with iodine in methanol solution yielded the depsipeptide FR901228.
| 【1】 Wang, H.-C. R.; FR901228. Drugs Fut 1999, 24, 11, 1184. |
| 【2】 Li, K.W.; Simon, J.A.; Xing, W.; Wu, J.; Total synthesis of the antitumor depsipeptide FR901228. J Am Chem Soc 1996, 118, 30, 7237. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (IV) | 29879 | methyl (2S)-2-[((Z)-2-[[(2S)-2-[[(2R)-2-amino-3-methylbutanoyl]amino]-3-(tritylsulfanyl)propanoyl]amino]-2-butenoyl)amino]-3-methylbutanoate | C37H46N4O5S | 详情 | 详情 | |
| (VIII) | 29884 | (3R,4E)-3-hydroxy-7-(tritylsulfanyl)-4-heptenoic acid | C26H26O3S | 详情 | 详情 | |
| (IX) | 29885 | (E,7R,11R,14S,20S)-17-[(Z)ethylidene]-7-hydroxy-11,20-diisopropyl-9,12,15,18-tetraoxo-1,1,1-triphenyl-14-[(tritylsulfanyl)methyl]-2-thia-10,13,16,19-tetraaza-5-henicosen-21-oic acid | C62H68N4O7S2 | 详情 | 详情 | |
| (X) | 29886 | (3S,9S,12R,16S)-6-[(Z)ethylidene]-3,12-diisopropyl-16-[(E)-4-(tritylsulfanyl)-1-butenyl]-9-[(tritylsulfanyl)methyl]-1-oxa-4,7,10,13-tetraazacyclohexadecane-2,5,8,11,14-pentone | C62H66N4O6S2 | 详情 | 详情 |