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【结 构 式】

【分子编号】47855

【品名】(2R,3S,4S)-4-([[tert-butyl(diphenyl)silyl]oxy]methyl)-3-(phenylselanyl)tetrahydro-2-furanol

【CA登记号】

【 分 子 式 】C27H32O3SeSi

【 分 子 量 】511.59478

【元素组成】C 63.39% H 6.3% O 9.38% Se 15.43% Si 5.49%

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:(Va)

Catalytic hydrogenation of dihydrofuranone (I) over Pd/C afforded the saturated lactone (II). Treatment of (II) with chlorotrimethylsilane and lithium hexamethyldisilazide produced the silyl enol ether (III) which, without isolation, was treated with phenylselenenyl bromide to yield the trans-selenide (IV). Lactone reduction by means of DIBAL followed by acetylation of the resulting lactol (Va-b) gave acetate (VIa-b). The glycosylation of the silylated fluorouracil (VII) with (VIa-b) in the presence of trimethylsilyl triflate furnished adduct (VIIIa-b). Subsequent oxidative elimination of the phenylselenenyl group of (VIIIa-b) via an intermediate selenoxide produced the dihydrofuran derivative (IX), which was finally desilylated by treatment with tetrabutylammonium fluoride.

1 Kim, H.O.; Moon, H.R.; Lee, C.-K.; Jeong, L.S.; Choi, W.J.; Chun, M.W.; Hong, J.H.; Yoo, S.J.; Synthesis and structure-activity relationships of novel apio and thioapio dideoxydidehydronucleosides as anti-HCMV agents. J Med Chem 2001, 44, 5, 806.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(Va) 47855 (2R,3S,4S)-4-([[tert-butyl(diphenyl)silyl]oxy]methyl)-3-(phenylselanyl)tetrahydro-2-furanol C27H32O3SeSi 详情 详情
(Vb) 47856 (2S,3S,4S)-4-([[tert-butyl(diphenyl)silyl]oxy]methyl)-3-(phenylselanyl)tetrahydro-2-furanol C27H32O3SeSi 详情 详情
(VIa) 47857 (2S,3S,4S)-4-([[tert-butyl(diphenyl)silyl]oxy]methyl)-3-(phenylselanyl)tetrahydro-2-furanyl acetate C29H34O4SeSi 详情 详情
(VIb) 47858 (2R,3S,4S)-4-([[tert-butyl(diphenyl)silyl]oxy]methyl)-3-(phenylselanyl)tetrahydro-2-furanyl acetate C29H34O4SeSi 详情 详情
(VIIIa) 47860 1-[(2R,3S,4S)-4-([[tert-butyl(diphenyl)silyl]oxy]methyl)-3-(phenylselanyl)tetrahydro-2-furanyl]-5-fluoro-2,4(1H,3H)-pyrimidinedione C31H33FN2O4SeSi 详情 详情
(VIIIb) 47861 1-[(2S,3S,4S)-4-([[tert-butyl(diphenyl)silyl]oxy]methyl)-3-(phenylselanyl)tetrahydro-2-furanyl]-5-fluoro-2,4(1H,3H)-pyrimidinedione C31H33FN2O4SeSi 详情 详情
(I) 47851 4-([[tert-butyl(diphenyl)silyl]oxy]methyl)-2(5H)-furanone C21H24O3Si 详情 详情
(II) 47852 4-([[tert-butyl(diphenyl)silyl]oxy]methyl)dihydro-2(3H)-furanone C21H26O3Si 详情 详情
(III) 47853 tert-butyl(diphenyl)silyl [5-[(trimethylsilyl)oxy]-2,3-dihydro-3-furanyl]methyl ether; [[4-([[tert-butyl(diphenyl)silyl]oxy]methyl)-4,5-dihydro-2-furanyl]oxy](trimethyl)silane C24H34O3Si2 详情 详情
(IV) 47854 (3S,4S)-4-([[tert-butyl(diphenyl)silyl]oxy]methyl)-3-(phenylselanyl)dihydro-2(3H)-furanone C27H30O3SeSi 详情 详情
(VII) 47859 5-fluoro-2-[(trimethylsilyl)oxy]-4-pyrimidinyl trimethylsilyl ether; 5-fluoro-2,4-bis[(trimethylsilyl)oxy]pyrimidine 17242-85-2 C10H19FN2O2Si2 详情 详情
(IX) 47862 1-[4-([[tert-butyl(diphenyl)silyl]oxy]methyl)-2,5-dihydro-2-furanyl]-5-fluoro-2,4(1H,3H)-pyrimidinedione C25H27FN2O4Si 详情 详情
Extended Information