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【结 构 式】 
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【分子编号】62935 【品名】(4R)-3-[(E)-2-butenoyl]-4-phenyl-1,3-oxazolidin-2-one 【CA登记号】 |
【 分 子 式 】C13H13NO3 【 分 子 量 】231.25116 【元素组成】C 67.52% H 5.67% N 6.06% O 20.76% |
合成路线1
该中间体在本合成路线中的序号：(I)Synthesis of the acetylenic dihydropyran intermediate (VII): The reaction of the chiral oxazolinone (I) with allylmagnesium bromide (II) by means of CuBr, BF3/Et2O and Mg(OMe)2, followed by ozonolysis with O3 in dichloromethane gives the aldehyde (III), which is condensed with the enol ether (IV) by means of a chiral Cr catalist to yield the dihydropyranone(V). The reduction of (V) with NaBH4 and CeCl3, followed by acylation with Ac2O affords the acetoxydihydropyran derivative (VI). Which is finally condensed with the allenic tributyl tin compound (VII) and trimethylsilylmethyl magnesium chloride in THF to provide the target acetylenic dihydropyran intermediate (VIII).
| 【1】 Williams, D.R.; et al.; Synthesis of (-)-laulimalide: An agent for microtubule stabilization. Tetrahedron Lett 2002, 43, 27, 4841. |
| 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) | 62935 | (4R)-3-[(E)-2-butenoyl]-4-phenyl-1,3-oxazolidin-2-one | C13H13NO3 | 详情 | 详情 | |
| (II) | 10386 | Allyl(bromo)magnesium | 1730-25-2 | C3H5BrMg | 详情 | 详情 |
| (III) | 62936 | Methyl (3R)-3-methyl-5-oxopentanoate | C7H12O3 | 详情 | 详情 | |
| (IV) | 62937 | {[(E)-3-methoxy-1-methylene-2-propenyl]oxy}(trimethyl)silane; (E)-3-methoxy-1-methylene-2-propenyl trimethylsilyl ether | C8H16O2Si | 详情 | 详情 | |
| (V) | 62938 | methyl (3R)-3-methyl-4-[(2R)-4-oxo-3,4-dihydro-2H-pyran-2-yl]butanoate | C11H16O4 | 详情 | 详情 | |
| (VI) | 62939 | methyl (3R)-4-[(2R,4S)-4-(acetyloxy)-3,4-dihydro-2H-pyran-2-yl]-3-methylbutanoate | C13H20O5 | 详情 | 详情 | |
| (VII) | 62940 | 2-[1,1'-biphenyl]-4-ylethyl 2-(tributylstannyl)-2,3-butadienyl ether; 4-(2-{[2-(tributylstannyl)-2,3-butadienyl]oxy}ethyl)-1,1'-biphenyl | C30H44OSn | 详情 | 详情 | |
| (VIII) | 62941 | 2-[1,1'-biphenyl]-4-ylethyl 4-((2R,6R)-6-{(2S)-2-methyl-4-[(trimethylsilyl)methyl]-4-pentenyl}-5,6-dihydro-2H-pyran-2-yl)-2-butynyl ether; 4-(2-{[4-((2R,6R)-6-{(2S)-2-methyl-4-[(trimethylsilyl)methyl]-4-pentenyl}-5,6-dihydro-2H-pyran-2-yl)-2-butynyl]oxy}ethyl)-1,1'-biphenyl | C33H44O2Si | 详情 | 详情 |