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【结 构 式】 
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【分子编号】60101 【品名】(4S)-4-benzyl-3-(5-hexenoyl)-1,3-oxazolidin-2-one 【CA登记号】 |
【 分 子 式 】C16H19NO3 【 分 子 量 】273.3318 【元素组成】C 70.31% H 7.01% N 5.12% O 17.56% |
与该中间体有关的原料药合成路线共 1 条
合成路线1
该中间体在本合成路线中的序号：(I)Chiral oxazolidinone intermediate (VI): The oxidation of the terminal double bond of the chiral acyl oxazolidinone (I) with O2 catalyzed by CuCl and PdCl2 in DMF/water gives the ketone (II), which is ketalized with propane-1,3-dithiol (III) and Ts-OH in AcOH to yield the thioketal (IV). Finally, the stereocontrolled acylation of (IV) with propionyl chloride (V) by means of LDA in THF affords the target oxazolidinone intermediate (VI)
| 【1】 Duan, M.S.; Paquette, L.A.; Highly diastereocontrolled synthesis of the C1-C25 domain of sanglifehrin A. Tetrahedron Lett 2000, 41, 20, 3789. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 60101 | (4S)-4-benzyl-3-(5-hexenoyl)-1,3-oxazolidin-2-one | C16H19NO3 | 详情 | 详情 | |
| (II) | 60102 | 1-[(4S)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-1,5-hexanedione | C16H19NO4 | 详情 | 详情 | |
| (III) | 29729 | 1,3-propanedithiol; 3-sulfanylpropylhydrosulfide | 109-80-8 | C3H8S2 | 详情 | 详情 |
| (IV) | 60103 | (4S)-4-benzyl-3-[4-(2-methyl-1,3-dithian-2-yl)butanoyl]-1,3-oxazolidin-2-one | C19H25NO3S2 | 详情 | 详情 | |
| (V) | 15967 | propanoyl chloride; propionyl chloride | 79-03-8 | C3H5ClO | 详情 | 详情 |
| (VI) | 60104 | (2R)-1-[(4S)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-2-[2-(2-methyl-1,3-dithian-2-yl)ethyl]-1,3-pentanedione | C22H29NO4S2 | 详情 | 详情 |
Extended Information