| (4S)-1-芴甲氧羰基-4-叠氮基-L-脯氨酸的合成 |
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| 引用本文： | 姚建忠,张万年,余建鑫,杨松,宋云龙,盛春泉.(4S)-1-芴甲氧羰基-4-叠氮基-L-脯氨酸的合成[J].中国药物化学杂志,2004,14(2):94-95,108. |
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| 作者姓名： | 姚建忠 张万年 余建鑫 杨松 宋云龙 盛春泉 |
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| 作者单位： | 第二军医大学药学院,上海,200433 |
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| 基金项目： | 国家高技术研究发展计划(863计划) |
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| 摘 要： | 目的合成用于caspofungin类似物全合成的关键中间体--(4S)-1-芴甲氧羰基-4-叠氮基-L-脯氨酸.方法以(4R)-1-叔丁氧羰基-4-羟基-L-脯氨酸乙酯(2)为原料,经羟基甲磺酰化、叠氮基取代、酯水解、氨基脱叔丁氧羰基保护及9-芴甲氧羰基再保护合成了关键氨基酸中间体(4S)-1-芴甲氧羰基-4-叠氮基-L-脯氨酸,通过质谱(MS)和氢谱(1H-NMR)确证其结构.结果该工艺反应条件温和、操作简便、收率高,总收率达62.3%.
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| 关 键 词： | 药物化学 工艺改进 甲磺酰化 取代 水解 缩合 (4S)-1-芴甲氧羰基-4-叠氮基-L-脯氨酸 |
| 文章编号： | 1005-0108(2004)02-0094-02 |
Synthesis of(4S)-1-fluorenylmethoxycarbonyl-4-azido-L-proline |
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| YAO Jian-zhong,ZHANG Wan-nian,YU Jian-xin,YANG Song,SONG Yun-long,SHENG Chun-quan.Synthesis of(4S)-1-fluorenylmethoxycarbonyl-4-azido-L-proline[J].Chinese Journal of Medicinal Chemistry,2004,14(2):94-95,108. |
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| Authors: | YAO Jian-zhong ZHANG Wan-nian YU Jian-xin YANG Song SONG Yun-long SHENG Chun-quan |
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| Abstract: | S)-1-fluorenylmethoxycarbonyl-4-azido-L-proline,a very important pharmaceutical intermediate for the synthesis of peptide drugs,was synthesized from(4R)-1-(tert-butoxycarbonyl)-4-hydroxy-L-proline ethyl ester via mesylation,azide displacement,hydrolysis and deprotected,followed by condensation with 9-fluorenylmethyl succinimidyl carbonate in an overall yield of 62.3%.Its structure was confirmed by 1H-NMR and MS spectra.The process developed has several adventages such as facile reaction conditions,convenient workup and high yield. |
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| Keywords: | medicinal chemistry process improvement mesylation displacement hydrolysis condensation (4S)-1-fluorenylmethoxycarbonyl-4-azido-L-proline |
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