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【结 构 式】 
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【分子编号】31985 【品名】methyl 3-azido-2-oxo-3-phenylpropanoate 【CA登记号】 |
【 分 子 式 】C10H9N3O3 【 分 子 量 】219.19988 【元素组成】C 54.79% H 4.14% N 19.17% O 21.9% |
合成路线1
该中间体在本合成路线中的序号：(III)A new synthesis of the side chain of paclitaxel has been described: The reaction of 2,3-epoxy-3-phenylpropionic acid methyl ester (I) with sodium azide in hot methanol/DMF/water gives 3-azido-2-hydroxy-3-phenylpropionic acid methyl ester (II), which is oxidized with Jones' reagent yielding 3-azido-2-oxo-3-phenylpropionic acid methyl ester (III). The reduction of (III) with Baker's yeast in water affords 3(RS)-azido-2(R)-hydroxy-3-phenylpropionic acid methyl ester (IV) as a diastereomeric mixture, which is resolved by spinning-plate chromatography in silicagel using ethyl acetate/pentane as solvent. The resulting (2R, 3S)-isomer (IV) is converted into the target compound by known methods (Adam, W. et al Tetrahedron Asymmetry, 1995, 6: 1047).
| 【1】 Kayser, M.M.; et al.; Baker's yeast-mediated reductions of alpha-keto esters and an alpha-keto-beta-lactam. Two routes to the paclitaxel side chain. J Org Chem 1999, 64, 18, 6603. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 31988 | (2R,3S)-3-(benzoylamino)-2-hydroxy-3-phenylpropionic acid | C16H15NO4 | 详情 | 详情 | ||
| (I) | 32007 | methyl 3-phenyl-2-oxiranecarboxylate | C10H10O3 | 详情 | 详情 | |
| (II) | 31984 | methyl 3-azido-2-hydroxy-3-phenylpropanoate | C10H11N3O3 | 详情 | 详情 | |
| (III) | 31985 | methyl 3-azido-2-oxo-3-phenylpropanoate | C10H9N3O3 | 详情 | 详情 | |
| (IV) | 31986 | methyl (2R)-3-azido-2-hydroxy-3-phenylpropanoate | C10H11N3O3 | 详情 | 详情 | |
| (V) | 31987 | methyl (2R,3S)-3-azido-2-hydroxy-3-phenylpropanoate | C10H11N3O3 | 详情 | 详情 |