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【结 构 式】

【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%

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:(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
Extended Information