Facile synthetic route to (2S,3S)-3-amino-2-hydroxy-4-phenylbutyric acid and its derivatives, the key intermediates for HIV protease inhibitors
文献类型：期刊论文
| 作者 | Lei, LJ; He, XC; Bai, DL
|
| 刊名 | SYNTHETIC COMMUNICATIONS
 |
| 出版日期 | 2005 |
| 卷号 | 35期号:11页码:1535-1540 |
| 关键词 | AHPBA HIV protease inhibitors Nagata's reagent N-phthaloyl protecting group |
| ISSN号 | 0039-7911 |
| DOI | 10.1081/SCC-200058003 |
| 文献子类 | Article |
| 英文摘要 | A facile and efficient route to (2S,3S)-3-amino-2-hydroxy-4-phenylbutyric acid and its derivative (4S,5S)-4-benzyl-5-hydroxymethyloxazolidin-2-one is presented. N-phthaloyl protected L-phenylalanine 1 was treated with thionyl chloride followed by hydrogenation of the acyl chloride 2 on Pd/C, giving (S)-2-phthalimido-3-phenylpropionaldehyde 3. Aldehyde 3 reacted with Nagata's reagent to afford 3-phthalimido-2-hydroxy-4-phenylbutyronitrile 4 as a diastereomeric mixture. After hydrolysis, protection, esterification, and reduction, 4 was transformed into the optically pure compound 7 in good yield. |
| WOS关键词 | BETA-AMINO ; ALDEHYDES |
| WOS研究方向 | Chemistry |
| 语种 | 英语 |
| WOS记录号 | WOS:000230107300014 |
| 出版者 | TAYLOR & FRANCIS INC |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/273973]  |
| 专题 | 中国科学院上海药物研究所 |
| 通讯作者 | Lei, LJ |
| 作者单位 | Chinese Acad Sci, Shanghai Inst Biol Sci, Shanghai Inst Mat Med, Shanghai 201203, Peoples R China |
| 推荐引用方式 GB/T 7714 | Lei, LJ,He, XC,Bai, DL. Facile synthetic route to (2S,3S)-3-amino-2-hydroxy-4-phenylbutyric acid and its derivatives, the key intermediates for HIV protease inhibitors[J]. SYNTHETIC COMMUNICATIONS,2005,35(11):1535-1540. |
| APA | Lei, LJ,He, XC,&Bai, DL.(2005).Facile synthetic route to (2S,3S)-3-amino-2-hydroxy-4-phenylbutyric acid and its derivatives, the key intermediates for HIV protease inhibitors.SYNTHETIC COMMUNICATIONS,35(11),1535-1540. |
| MLA | Lei, LJ,et al."Facile synthetic route to (2S,3S)-3-amino-2-hydroxy-4-phenylbutyric acid and its derivatives, the key intermediates for HIV protease inhibitors".SYNTHETIC COMMUNICATIONS 35.11(2005):1535-1540. |
入库方式： OAI收割
来源：上海药物研究所
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