2-([(1R)-1-[2-(2,4-difluorophenyl)-2-oxiranyl]ethyl]oxy)tetrahydro-2H-pyran -Drug Synthesis Database

【结构式】

【分子编号】27882

【品名】2-([(1R)-1-[2-(2,4-difluorophenyl)-2-oxiranyl]ethyl]oxy)tetrahydro-2H-pyran

【CA登记号】

【分子式】C₁₅H₁₈F₂O₃

【分子量】284.3029264

【元素组成】C 63.37% H 6.38% F 13.36% O 16.88%

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：(VIa)

The diastereomeric mixture of tetrahydropyranyl-protected compounds (VI) was hydrolyzed with pyridinium p-toluenesulfonate to furnish the epoxyalcohols (VII). Subsequent coupling of (VIII) with 3,5-dinitrobenzoyl chloride produced a mixture of diastereomeric esters, from which the required isomer (VIII) was isolated by recrystallization from EtOAc. Hydrolysis with methanolic NaOH yielded the R,R-epoxyalcohol (IX). Inversion of configuration was then achieved by Mitsunobu coupling with benzoic acid, followed by hydrolysis of the resulting benzoate ester (X).

参考文献中间体

合成目标

【1】 Itoh, K.; Tamura, N.; Matsushita, Y.; Hososno, H.; Hayashi, R.; Okonogi, K.; Kitazaki, T.; Tasaka, A.; Optically active antifungal azoles. VIII. Synthesis and antifungal activity of 1-[(1R,2R)-2-(2,4-difluoro- and 2-fluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]-3-(4-substituted phenyl)-2(1H,3H)-imidazolones and 2-imidazolidinones. Chem Pharm Bull 1999, 47, 3, 351.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(VIIa)	27873	(1R)-1-[2-(2,4-difluorophenyl)-2-oxiranyl]-1-ethanol		C₁₀H₁₀F₂O₂	详情	详情
(VIa)	27882	2-([(1R)-1-[2-(2,4-difluorophenyl)-2-oxiranyl]ethyl]oxy)tetrahydro-2H-pyran		C₁₅H₁₈F₂O₃	详情	详情
(VIIb)	53869	(1R)-1-[(2R)-2-(2,4-difluorophenyl)oxiranyl]-1-ethanol	n/a	C₁₀H₁₀F₂O₂	详情	详情
(VIb)	53870	2-({(1R)-1-[(2R)-2-(2,4-difluorophenyl)oxiranyl]ethyl}oxy)tetrahydro-2H-pyran; (1R)-1-[(2R)-2-(2,4-difluorophenyl)oxiranyl]ethyl tetrahydro-2H-pyran-2-yl ether	n/a	C₁₅H₁₈F₂O₃	详情	详情
(VIII)	27874	(1R)-1-[(2R)-2-(2,4-difluorophenyl)oxiranyl]ethyl 3,5-dinitrobenzoate		C₁₇H₁₂F₂N₂O₇	详情	详情
(IX)	27875	(1R)-1-[(2R)-2-(2,4-difluorophenyl)oxiranyl]-1-ethanol		C₁₀H₁₀F₂O₂	详情	详情
(X)	27876	(1S)-1-[(2R)-2-(2,4-difluorophenyl)oxiranyl]ethyl benzoate		C₁₇H₁₄F₂O₃	详情	详情
(XI)	27877	(1S)-1-[(2R)-2-(2,4-difluorophenyl)oxiranyl]-1-ethanol		C₁₀H₁₀F₂O₂	详情	详情

Extended Information