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【结 构 式】 
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【分子编号】47340 【品名】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 【CA登记号】 |
【 分 子 式 】C33H44N6O11 【 分 子 量 】700.7462 【元素组成】C 56.56% H 6.33% N 11.99% O 25.12% |
合成路线1
该中间体在本合成路线中的序号：(XII)The cyclic peptide precursor (XIV) was prepared by solid-phase synthesis on a preformed HMPB-MBHA resin. Attachment of N-Fmoc-glycine (I) to the resin by means of DCC and DMAP afforded resin (II). The Fmoc protecting group was then removed with piperidine in DMF, yielding the glycine-bound resin (III). Further couplings with the following protected amino acids: N-Fmoc-3-(aminomethyl)-5-nitrobenzoic acid (IV), N-Fmoc-L-tyrosine(O-t-butyl) (VI) and N-Fmoc-glycine (I), followed by Fmoc deprotection cycles, produced in turn the peptide resins (V), (VII) and (VIII). To peptide resin (VIII) was then coupled N-Fmoc-L-aspartic acid gamma-t-butyl ester (IX), yielding resin (X). Peptide (XI) was then liberated from the resin by means of 1% trifluoroacetic acid in CH2Cl2. The Fmoc group was subsequently removed by treatment with diethylamine in acetonitrile, giving (XII).
| 【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 |
|---|---|---|---|---|---|---|
| (I),(II) | 42131 | 2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]acetic acid | 29022-11-5 | C17H15NO4 | 详情 | 详情 |
| (X),(XI) | 47339 | 2-([3-[(4S,10S)-4-[4-(tert-butoxy)benzyl]-10-[2-(tert-butoxy)-2-oxoethyl]-14-(9H-fluoren-9-yl)-3,6,9,12-tetraoxo-13-oxa-2,5,8,11-tetraazatetradec-1-yl]-5-nitrobenzoyl]amino)acetic acid | C48H54N6O13 | 详情 | 详情 | |
| (III) | 20436 | glycine | 56-40-6 | C2H5NO2 | 详情 | 详情 |
| (IV) | 47335 | 3-([[(9H-fluoren-9-ylmethoxy)carbonyl]amino]methyl)-5-nitrobenzoic acid | C23H18N2O6 | 详情 | 详情 | |
| (V) | 47336 | 2-[[3-(aminomethyl)-5-nitrobenzoyl]amino]acetic acid | C10H11N3O5 | 详情 | 详情 | |
| (VI) | 18858 | (2S)-3-[4-(tert-butoxy)phenyl]-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]propionic acid | C28H29NO5 | 详情 | 详情 | |
| (VII) | 47337 | 2-([3-[([(2S)-2-amino-3-[4-(tert-butoxy)phenyl]propanoyl]amino)methyl]-5-nitrobenzoyl]amino)acetic acid | C23H28N4O7 | 详情 | 详情 | |
| (VIII) | 47338 | 2-([3-[([(2S)-2-[(2-aminoacetyl)amino]-3-[4-(tert-butoxy)phenyl]propanoyl]amino)methyl]-5-nitrobenzoyl]amino)acetic acid | C25H31N5O8 | 详情 | 详情 | |
| (IX) | 22260 | (2S)-4-(tert-butoxy)-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-4-oxobutyric acid | C23H25NO6 | 详情 | 详情 | |
| (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 |
合成路线2
该中间体在本合成路线中的序号：(XII)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 |