(4R,5S)-4-methyl-3-[(2S,4E)-2-methyl-5-phenyl-4-pentenoyl]-5-phenyl-1,3-oxazolidin-2-one -Drug Synthesis Database

【结构式】

【分子编号】46164

【品名】(4R,5S)-4-methyl-3-[(2S,4E)-2-methyl-5-phenyl-4-pentenoyl]-5-phenyl-1,3-oxazolidin-2-one

【CA登记号】

【分子式】C₂₂H₂₃NO₃

【分子量】349.42956

【元素组成】C 75.62% H 6.63% N 4.01% O 13.74%

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)

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).

参考文献中间体

合成目标

【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