| (2S, 3S)-3-氨基-2-羟基-4-苯丁酰胺的合成 |
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| 引用本文： | 张 勇,翟 鑫,李龙燮,宫 平.(2S, 3S)-3-氨基-2-羟基-4-苯丁酰胺的合成[J].中国药物化学杂志,2009,19(2):112-115. |
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| 作者姓名： | 张 勇 翟 鑫 李龙燮 宫 平 |
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| 作者单位： | （1．沈阳药科大学 制药工程学院，辽宁 沈阳 110016；2．庆熙大学 药学院 韩国 首尔 130-701） |
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| 摘 要： | 目的 合成α-酮基酰胺肽类钙蛋白酶抑制剂的必需结构片段 (2S, 3S)-3-氨基-2-羟基-4-苯丁酰胺（1）。 方法 以(S)-2-氨基-3-苯丙醇为起始原料，经过苄基保护、Parikh-Doering 氧化、氰化水解、酰胺化和脱保护共5步反应合成目标化合物。结果与讨论 目标化合物和中间体的结构均经1H-NMR和13C-NMR谱确证，该合成路线方法简捷，适于大量制备。
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| 关 键 词： | (2S 3S)-3-氨基-2-羟基-4-苯丁酰胺 钙蛋白酶抑制剂 α-酮基酰胺肽 合成 |
| 收稿时间： | 2008-7-22 |
| 修稿时间： | 2009-1-20 |
Synthesis of (2S, 3S)-3-amino-2-hydroxy-4-phenylbutanamide |
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| ZHANG Yong,ZHAI Xin,LEE Yong-sup,GONG Ping.Synthesis of (2S, 3S)-3-amino-2-hydroxy-4-phenylbutanamide[J].Chinese Journal of Medicinal Chemistry,2009,19(2):112-115. |
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| Authors: | ZHANG Yong ZHAI Xin LEE Yong-sup GONG Ping |
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| Institution: | (1. School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Shenyang 110016, China; 2. College of Pharmacy, Kyung Hee University, Seoul 130-701, Korea) |
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| Abstract: | Aim To synthesize (2S,3S)-3-amino-2-hydroxy-4-phenylbutanamide as the key intermediate of peptidyl α-ketoamides calpain inhibitors. Methods The targeted compound was synthesized from (S)-2-amino-3-phenylpropan-1-ol via 5 steps reactions including benzyl protection, Parikh-Doering oxidation, cyanohydrination and hydroxlyzation, amidation, and benzyl deprotection. Result and conclusion The structures of title compound and the intermediates were confirmed by 1H-NMR and 13C-NMR, and the synthetic route was concise compared with the reported one. |
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| Keywords: | (2S 3S)-3-amino-2-hydroxy-4-phenylbutanamide calpain inhibitors peptidyl α-ketoamides synthesis |
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