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【结 构 式】

【分子编号】61207

【品名】2-((2R,6S)-6-{(2R)-3-[(4-methoxybenzyl)oxy]-2-methylpropyl}-5,6-dihydro-2H-pyran-2-yl)acetaldehyde

【CA登记号】

【 分 子 式 】C19H26O4

【 分 子 量 】318.41304

【元素组成】C 71.67% H 8.23% O 20.1%

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:(XIV)

The synthesis of the dihydropyran intermediate (XX) has been performed as follows: The reduction of the known aldehyde (XIV) with NaBH4 in methanol, followed by reaction with Tbdms-Cl and imidazole in DMF gives the silyl ether (XV), which is selectively deprotected with DDQ in dichloromethane and treated with TsCl and TEA to yield the tosylate (XVI). The reaction of (XVI) with NaCN in hot DMSO, followed by reaction with MeLi in ethyl ether affords the methyl ketone (XVII), which is treated with KHMDS and Ph-NTf2 in THF to provide the enol triflate (XVIII). Finally, this compound is treated with Tms-CH2-MgCl , Pd(PPh3)4 and LiCl in ethyl ether to furnish the target dihydropyran intermediate (XX).

1 Mulzer, J.; Hanbauer, M.; Total synthesis of the antitumor agent (-)-laulimalide. Tetrahedron Lett 2002, 43, 18, 3381.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XIV) 61207 2-((2R,6S)-6-{(2R)-3-[(4-methoxybenzyl)oxy]-2-methylpropyl}-5,6-dihydro-2H-pyran-2-yl)acetaldehyde C19H26O4 详情 详情
(XV) 61208 tert-butyl(dimethyl)silyl 2-((2R,6S)-6-{(2R)-3-[(4-methoxybenzyl)oxy]-2-methylpropyl}-5,6-dihydro-2H-pyran-2-yl)ethyl ether; tert-butyl[2-((2R,6S)-6-{(2R)-3-[(4-methoxybenzyl)oxy]-2-methylpropyl}-5,6-dihydro-2H-pyran-2-yl)ethoxy]dimethylsilane C25H42O4Si 详情 详情
(XVI) 61301 (2R)-3-[(2S,6R)-6-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-3,6-dihydro-2H-pyran-2-yl]-2-methylpropyl 4-methylbenzenesulfonate C24H40O5SSi 详情 详情
(XVII) 61302 (4R)-5-[(2R,6R)-6-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-3,6-dihydro-2H-pyran-2-yl]-4-methyl-2-pentanone C19H36O3Si 详情 详情
(XVIII) 61303 1-{(2R)-3-[(2R,6R)-6-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-3,6-dihydro-2H-pyran-2-yl]-2-methylpropyl}vinyl trifluoromethanesulfonate C20H35F3O5SSi 详情 详情
(XIX) 61304 Trimethylsilylmethylmagnesium Chloride; (Trimethylsilyl)methylmagnesium chloride Solution; Chloro[(trimethylsilyl)methyl]magnesium; (TRIMETHYLSILYLMETHYL)MAGNESIUM CHLORIDE; (TRIMETHYLSILYL)METHYLMAGNESIUM CHL. SOL 13170-43-9 C4H11ClMgSi 详情 详情
(XX) 61305 tert-butyl(dimethyl)[2-((2R,6R)-6-{(2S)-2-methyl-4-[(trimethylsilyl)methyl]-4-pentenyl}-5,6-dihydro-2H-pyran-2-yl)ethoxy]silane; tert-butyl(dimethyl)silyl 2-((2R,6R)-6-{(2S)-2-methyl-4-[(trimethylsilyl)methyl]-4-pentenyl}-5,6-dihydro-2H-pyran-2-yl)ethyl ether C23H46O2Si2 详情 详情
Extended Information