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【结 构 式】 
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【分子编号】47353 【品名】25,26,27,28-tetrabutoxypentacyclo[19.3.1.1(3,7).1(9,13).1(15,19)]octacosa-1(25),3(28),4,6,9(27),10,12,15(26),16,18,21,23-dodecaene-5,11,17,23-tetracarbonyl tetrachloride 【CA登记号】 |
【 分 子 式 】C48H52Cl4O8 【 分 子 量 】898.74688 【元素组成】C 64.15% H 5.83% Cl 15.78% O 14.24% |
合成路线1
该中间体在本合成路线中的序号：(XXVI)Calix[4]arene (XXI) was alkylated with n-butyl bromide (XXII) and NaH to produce the tetrabutyl ether (XXIII). Formylation of (XXIII) with dichloromethyl methyl ether and TiCl4 yielded the aldehyde (XXIV), which was further oxidized to the tetracarboxylic acid (XXV) using sodium chlorite. Then, treatment of (XXV) with oxalyl chloride and DMF gave the corresponding acid chloride (XXVI).
| 【1】 Lin, Q.; et al.; Protein surface recognition by synthetic receptors. NATO ASI Series. Series C: Mathematical and Physical Sciences 1999, 527, 197. |
| 【2】 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 |
|---|---|---|---|---|---|---|
| (XXI) | 47349 | pentacyclo[19.3.1.1(3,7).1(9,13).1(15,19)]octacosa-1(25),3(28),4,6,9(27),10,12,15(26),16,18,21,23-dodecaene-25,26,27,28-tetrol | 74568-07-3 | C28H24O4 | 详情 | 详情 |
| (XXII) | 28721 | 1-bromobutane | 109-65-9 | C4H9Br | 详情 | 详情 |
| (XXIII) | 47350 | butyl 26,27,28-tributoxypentacyclo[19.3.1.1(3,7).1(9,13).1(15,19)]octacosa-1(25),3(28),4,6,9(27),10,12,15(26),16,18,21,23-dodecaen-25-yl ether; 25,26,27,28-tetrabutoxypentacyclo[19.3.1.1(3,7).1(9,13).1(15,19)]octacosa-1(25),3(28),4,6,9(27),10,12,15(26),16,18,21,23-dodecaene | C44H56O4 | 详情 | 详情 | |
| (XXIV) | 47351 | 25,26,27,28-tetrabutoxypentacyclo[19.3.1.1(3,7).1(9,13).1(15,19)]octacosa-1(25),3(28),4,6,9(27),10,12,15(26),16,18,21,23-dodecaene-5,11,17,23-tetracarbaldehyde | C48H56O8 | 详情 | 详情 | |
| (XXV) | 47352 | 25,26,27,28-tetrabutoxypentacyclo[19.3.1.1(3,7).1(9,13).1(15,19)]octacosa-1(25),3(28),4,6,9(27),10,12,15(26),16,18,21,23-dodecaene-5,11,17,23-tetracarboxylic acid | C48H56O12 | 详情 | 详情 | |
| (XXVI) | 47353 | 25,26,27,28-tetrabutoxypentacyclo[19.3.1.1(3,7).1(9,13).1(15,19)]octacosa-1(25),3(28),4,6,9(27),10,12,15(26),16,18,21,23-dodecaene-5,11,17,23-tetracarbonyl tetrachloride | C48H52Cl4O8 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(XXVI)Coupling of the cyclic peptide (XIV) with tetraacid chloride (XXVI) produced the corresponding tetraamide. The O-tert-butyl groups were then removed by treatment with trifluoroacetic acid to produce the title compound.
| 【1】 Lin, Q.; et al.; Protein surface recognition by synthetic receptors. NATO ASI Series. Series C: Mathematical and Physical Sciences 1999, 527, 197. |
| 【2】 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 |
|---|---|---|---|---|---|---|
| (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 | |
| (XXVI) | 47353 | 25,26,27,28-tetrabutoxypentacyclo[19.3.1.1(3,7).1(9,13).1(15,19)]octacosa-1(25),3(28),4,6,9(27),10,12,15(26),16,18,21,23-dodecaene-5,11,17,23-tetracarbonyl tetrachloride | C48H52Cl4O8 | 详情 | 详情 |