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【结 构 式】 
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【分子编号】47341 【品名】tert-butyl 2-[(7S,13S)-13-[4-(tert-butoxy)benzyl]-19-nitro-2,5,8,11,14-pentaoxo-3,6,9,12,15-pentaazabicyclo[15.3.1]henicosa-1(21),17,19-trien-7-yl]acetate 【CA登记号】 |
【 分 子 式 】C33H42N6O10 【 分 子 量 】682.73092 【元素组成】C 58.06% H 6.2% N 12.31% O 23.43% |
合成路线1
该中间体在本合成路线中的序号：(XIII)Compound (XII) was cyclized to (XIII) employing BOP and HOBt. The nitro group was then reduced to the corresponding amino derivative (XIV) by catalytic hydrogenation over Pd/C.
| 【1】 Park, H.S.; et al.; Protein surface recognition by synthetic receptors: A route to novel submicromolar inhibitors for alpha-chymotrypsin. J Am Chem Soc 1999, 121, 1, 8. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XII) | 47340 | 2-[(3-[(4S,10S)-10-amino-4-[4-(tert-butoxy)benzyl]-14,14-dimethyl-3,6,9,12-tetraoxo-13-oxa-2,5,8-triazapentadec-1-yl]-5-nitrobenzoyl)amino]acetic acid | C33H44N6O11 | 详情 | 详情 | |
| (XIII) | 47341 | tert-butyl 2-[(7S,13S)-13-[4-(tert-butoxy)benzyl]-19-nitro-2,5,8,11,14-pentaoxo-3,6,9,12,15-pentaazabicyclo[15.3.1]henicosa-1(21),17,19-trien-7-yl]acetate | C33H42N6O10 | 详情 | 详情 | |
| (XIV) | 47342 | tert-butyl 2-[(7S,13S)-19-amino-13-[4-(tert-butoxy)benzyl]-2,5,8,11,14-pentaoxo-3,6,9,12,15-pentaazabicyclo[15.3.1]henicosa-1(21),17,19-trien-7-yl]acetate | C33H44N6O8 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(XIII)In an alternative method for the solution-phase synthesis of this intermediate, methyl 3-carbamoyl-5-nitrobenzoate (XV) was reduced with borane to amino ester (XVI), which was subsequently hydrolyzed to the corresponding amino acid (XVII). Coupling of amino acid (XVII) with N-Fmoc-L-tyrosine(O-t-butyl) (VI) using DCC and N-hydroxysuccinimide produced dipeptide (XVIII). This was then coupled with the tripeptide H-Gly-Asp(t-Bu)-Gly-OH (XIX) to yield the linear peptide (XX). After Fmoc deprotection, cyclization in the presence of TBTU and DMAP furnished the cyclic peptide (XIII), which was further reduced to the amino derivative (XIV) as above.
| 【1】 Lin, Q.; et al.; Protein surface recognition by synthetic receptors. NATO ASI Series. Series C: Mathematical and Physical Sciences 1999, 527, 197. |
| 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) | 18858 | (2S)-3-[4-(tert-butoxy)phenyl]-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]propionic acid | C28H29NO5 | 详情 | 详情 | |
| (XIII) | 47341 | tert-butyl 2-[(7S,13S)-13-[4-(tert-butoxy)benzyl]-19-nitro-2,5,8,11,14-pentaoxo-3,6,9,12,15-pentaazabicyclo[15.3.1]henicosa-1(21),17,19-trien-7-yl]acetate | C33H42N6O10 | 详情 | 详情 | |
| (XV) | 47343 | methyl 3-(aminocarbonyl)-5-nitrobenzoate | C9H8N2O5 | 详情 | 详情 | |
| (XVI) | 47344 | methyl 3-(aminomethyl)-5-nitrobenzoate | C9H10N2O4 | 详情 | 详情 | |
| (XVII) | 47345 | 3-(aminomethyl)-5-nitrobenzoic acid | C8H8N2O4 | 详情 | 详情 | |
| (XVIII) | 47346 | 3-[[((2S)-3-[4-(tert-butoxy)phenyl]-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]propanoyl)amino]methyl]-5-nitrobenzoic acid | C36H35N3O8 | 详情 | 详情 | |
| (XIX) | 47347 | 2-[[(2S)-2-[(2-aminoacetyl)amino]-4-(tert-butoxy)-4-oxobutanoyl]amino]acetic acid | C12H21N3O6 | 详情 | 详情 | |
| (XX) | 47348 | 2-[[(2S)-4-(tert-butoxy)-2-([2-[(3-[[((2S)-3-[4-(tert-butoxy)phenyl]-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]propanoyl)amino]methyl]-5-nitrobenzoyl)amino]acetyl]amino)-4-oxobutanoyl]amino]acetic acid | C48H54N6O13 | 详情 | 详情 |