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【结 构 式】

【分子编号】46165

【品名】(2S,4E)-2-methyl-5-phenyl-4-penten-1-ol

【CA登记号】

【 分 子 式 】C12H16O

【 分 子 量 】176.25844

【元素组成】C 81.77% H 9.15% O 9.08%

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:(IV)

Synthesis of intermediate triphenylphosphonium salt (VII): The condensation of the chiral oxazolidinone (I) with cinnamyl bromide (II) by means of NaHMDS in THF gives the adduct (III), which is treated with LiBH4 in Et2O/water to yield the alcohol (IV). The protection of (IV) with Tbdms-Cl and imidazole in DMF affords the silyl ether (V), which is treated with ozone and reduced with NaBH4 to provide the alcohol (VI). The reaction of (VI) with I2 and PPh3 gives the desired triphenylphosphonium iodide (VII).

1 Mulzer, J.; et al.; A novel highly stereoselective total synthesis of epothilone B and of its (12R,13R) acetonide. Tetrahedron Lett 2000, 41, 40, 7635.
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) 46163 (4R,5S)-4-methyl-5-phenyl-3-propionyl-1,3-oxazolidin-2-one C13H15NO3 详情 详情
(II) 21131 1-[(E)-3-bromo-1-propenyl]benzene 4392-24-9 C9H9Br 详情 详情
(III) 46164 (4R,5S)-4-methyl-3-[(2S,4E)-2-methyl-5-phenyl-4-pentenoyl]-5-phenyl-1,3-oxazolidin-2-one C22H23NO3 详情 详情
(IV) 46165 (2S,4E)-2-methyl-5-phenyl-4-penten-1-ol C12H16O 详情 详情
(V) 46166 tert-butyl(dimethyl)silyl (2S,4E)-2-methyl-5-phenyl-4-pentenyl ether; tert-butyl(dimethyl)[[(2S,4E)-2-methyl-5-phenyl-4-pentenyl]oxy]silane C18H30OSi 详情 详情
(VI) 46167 (3S)-4-[[tert-butyl(dimethyl)silyl]oxy]-3-methyl-1-butanol C11H26O2Si 详情 详情
(VII) 46168 ((3S)-4-[[tert-butyl(dimethyl)silyl]oxy]-3-methylbutyl)(triphenyl)phosphonium iodide C29H40IOPSi 详情 详情
Extended Information