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                当前地位: edf壹定发888 » 材料 » 医药中心体库 » ,C17H17NO4,299.3293,(2R)-3-Phenyl-2-[[(2-phenylacetyl)oxy]am

                ,C17H17NO4,299.3293,(2R)-3-Phenyl-2-[[(2-phenylacetyl)oxy]am

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                壹定发老虎机娱乐平台:,C17H17NO4,299.3293,(2R)-3-Phenyl-2-[[(2-phenylacetyl)oxy]amino]propionic acid
                • 【化学名】(2R)-3-Phenyl-2-[[(2-phenylacetyl)oxy]amino]propionic acid
                • 【CAS挂号号】
                • 【构造式】,C17H17NO4,299.3293,(2R)-3-Phenyl-2-[[(2-phenylacetyl)oxy]am--药物合成数据库
                • 【份子式】C17H17NO4
                • 【份子量】299.3293
                • 【来源】
                • 【合成情况】 
                • 〖目标产品〗Efegatran sulfate hydrate, LY-294468, GYKI-14766
                • 〖合成线路〗
                • 〖合成办法〗The synthesis of GYKI-14766 is as follows: N2-tert-Butoxycarbonyl-L-arginine (I) was converted to the N6-benzyloxycarbonyl derivative (II). Treatment of (II) with isobutoxycarbonyl chloride and N-methylmorpholine gave the aminolactam (III). Dicyclohexylcarbodiimide-mediated esterification of N-benzyloxycarbonyl-D-phenylalanine (IV) with 2,4,5-trichlorophenol gave the active ester (V), which was coupled with L-proline to the dipeptide (VI). Methylation with iodomethane afforded the N-methyl derivative isolated as the cyclohexylamine salt (VII). The fragments (III) and (VII) were coupled via the mixed anhydride of (VII), generated as in the case of (II), giving the tripeptide lactam (VIII). Reduction with lithium aluminum hydride at low temperature converted (VIII) to the aldehyde (IX), which was finally deprotected to the end product.
                • 〖参考〗Szll, E.; Bagdy, D.; Bajusz, S.; et al.; Highly active and selective anticoagulants: D-Phe-Pro-Arg-H, a free tripeptide aldehyde prone to spontaneous inactivation and its stable N-methyl derivative, D-MePhe-Pro-Arg-H. J Med Chem 1990, 33, 6, 1729-35
                • 〖目标产品〗Efegatran sulfate hydrate, LY-294468, GYKI-14766
                • 〖合成线路〗
                • 〖合成办法〗The synthesis of GYKI-14766 is as follows: N2-tert-Butoxycarbonyl-L-arginine (I) was converted to the N6-benzyloxycarbonyl derivative (II). Treatment of (II) with isobutoxycarbonyl chloride and N-methylmorpholine gave the aminolactam (III). Dicyclohexylcarbodiimide-mediated esterification of N-benzyloxycarbonyl-D-phenylalanine (IV) with 2,4,5-trichlorophenol gave the active ester (V), which was coupled with L-proline to the dipeptide (VI). Methylation with iodomethane afforded the N-methyl derivative isolated as the cyclohexylamine salt (VII). The fragments (III) and (VII) were coupled via the mixed anhydride of (VII), generated as in the case of (II), giving the tripeptide lactam (VIII). Reduction with lithium aluminum hydride at low temperature converted (VIII) to the aldehyde (IX), which was finally deprotected to the end product.
                • 〖参考〗Ngradi, M.; GYKI-14766. Drugs Fut 1992, 17, 12, 1087
                 
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