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【结 构 式】 
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【分子编号】32398 【品名】dibenzyl (9S,12S,17S,20S)-12,17-diamino-3,11,18,26-tetraoxo-1,28-diphenyl-2,27-dioxa-4,10,19,25-tetraazaoctacosane-9,20-dicarboxylate 【CA登记号】 |
【 分 子 式 】C50H64N6O10 【 分 子 量 】909.0926 【元素组成】C 66.06% H 7.1% N 9.24% O 17.6% |
合成路线1
该中间体在本合成路线中的序号：(VI)The Kolbe electrolysis of N-(tert-butoxycarbonyl)-L-glutamic acid 1-O-benzyl ester (I) gives 2(S),7(S)-bis(tert-butoxycarbonylamino)octanedioic acid dibenzyl ester (II), which is debenzylated with H2 over Pd/C in methanol yielding the free acid (III). The condensation of diacid (III) with N6-(benzyloxycarbonyl)-L-lysine benzyl ester (IV) affords the tripeptide (V), which is then treated with HCl in dioxane to eliminate the carbamate protecting groups so providing intermediate (VI).
| 【1】 Hiebl, J.; et al.; Large-scale synthesis of hematoregulatory nonapeptide SK&F 107647 by fragment coupling. J Pept Res 1999, 54, 1, 54. |
| 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) | 10136 | (4R)-5-(Benzyloxy)-4-[(tert-butoxycarbonyl)amino]-5-oxopentanoic acid; N-t-BOC-D-glutamic acid alpha-benzyl ester | 34404-30-3 | C17H23NO6 | 详情 | 详情 |
| (II) | 32394 | dibenzyl (2S,7S)-2,7-bis[(tert-butoxycarbonyl)amino]octanedioate | C32H44N2O8 | 详情 | 详情 | |
| (III) | 32395 | (2S,7S)-2,7-bis[(tert-butoxycarbonyl)amino]octanedioic acid | C18H32N2O8 | 详情 | 详情 | |
| (IV) | 32396 | benzyl (2S)-2-amino-6-[[(benzyloxy)carbonyl]amino]hexanoate | C21H26N2O4 | 详情 | 详情 | |
| (V) | 32397 | dibenzyl (9S,12S,17S,20S)-12,17-bis[(tert-butoxycarbonyl)amino]-3,11,18,26-tetraoxo-1,28-diphenyl-2,27-dioxa-4,10,19,25-tetraazaoctacosane-9,20-dicarboxylate | C60H80N6O14 | 详情 | 详情 | |
| (VI) | 32398 | dibenzyl (9S,12S,17S,20S)-12,17-diamino-3,11,18,26-tetraoxo-1,28-diphenyl-2,27-dioxa-4,10,19,25-tetraazaoctacosane-9,20-dicarboxylate | C50H64N6O10 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(VI)The condensation of tripeptide (XV) with intermediate tripeptide (VI) by means of TDBTU and DIEA in DMF gives the fully benzylated target compound, which is finally deprotected with H2 over Pd/C in DMF/AcOH.
| 【1】 Hiebl, J.; et al.; Large-scale synthesis of hematoregulatory nonapeptide SK&F 107647 by fragment coupling. J Pept Res 1999, 54, 1, 54. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (VI) | 32398 | dibenzyl (9S,12S,17S,20S)-12,17-diamino-3,11,18,26-tetraoxo-1,28-diphenyl-2,27-dioxa-4,10,19,25-tetraazaoctacosane-9,20-dicarboxylate | C50H64N6O10 | 详情 | 详情 | |
| (XV) | 32404 | (2S)-4-(benzyloxy)-2-[[(2S)-5-(benzyloxy)-5-oxo-2-([[(2S)-5-oxopyrrolidinyl]carbonyl]amino)pentanoyl]amino]-4-oxobutyric acid | C28H31N3O9 | 详情 | 详情 | |
| (XVI) | 32405 | dibenzyl (4S,7S,10S,15S,18S,21S)-10,15-bis{[((1S)-1-[(benzyloxy)carbonyl]-5-{[(benzyloxy)carbonyl]amino}pentyl)amino]carbonyl}-7,18-bis[2-(benzyloxy)-2-oxoethyl]-5,8,17,20-tetraoxo-4,21-bis({[(2S)-5-oxopyrrolidinyl]carbonyl}amino)-6,9,16,19-tetraazatetracosane-1,24-dioate | C106H122N12O26 | 详情 | 详情 |