4-Amino-1-((2R,3R,4R,5R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-methyltetrahydro-2-furanyl)-5-fluoro-2(1H)-pyrimidinone -Drug Synthesis Database

【结构式】

【分子编号】13570

【品名】4-Amino-1-((2R,3R,4R,5R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-methyltetrahydro-2-furanyl)-5-fluoro-2(1H)-pyrimidinone

【CA登记号】

【分子式】C₂₁H₄₀FN₃O₄Si₂

【分子量】473.7358232

【元素组成】C 53.24% H 8.51% F 4.01% N 8.87% O 13.51% Si 11.86%

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：(II)

The silylation of 5'-deoxy-5-fluorocytidine (I) with tert-butyldimethylsilyl chloride and imidazole in DMF gives 2'-O,3'-O-bis(tert-butyldimethylsilyl)-5'-deoxy-5-fluorocytidine (II), which is acylated with 3,4,5-trimethoxybenzoyl chloride (III) and dimethylaminopyridine in dichloromethane to afford 2'-O,3'-O-bis(tert-butyldimethylsilyl)-5'-deoxy-5-fluoro-N4-(3,4,5-trimethoxybenzoyl)cytidine (IV). Finally, this compound is deprotected with tetrabutylammonium fluoride in THF.

参考文献中间体

合成目标

【1】 Fujiu, M.; Ishitsuka, H.; Miwa, M.; Umeda, I.; Yokose, K. (F. Hoffmann-La Roche AG); Fluorocytidine derivs., their preparation and medical preparations containing them. AU 8825168; EP 0316704; JP 1989153696; US 4966891 .
【2】 Hoshi, A.; Castaner, J.; Galocitabine. Drugs Fut 1993, 18, 4, 316.

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)	13569	4-Amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyltetrahydro-2-furanyl]-5-fluoro-2(1H)-pyrimidinone		C₉H₁₂FN₃O₄	详情	详情
(II)	13570	4-Amino-1-((2R,3R,4R,5R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-methyltetrahydro-2-furanyl)-5-fluoro-2(1H)-pyrimidinone		C₂₁H₄₀FN₃O₄Si₂	详情	详情
(III)	13571	3,4,5Ttrimethoxybenzoyl chloride	4521-61-3	C₁₀H₁₁ClO₄	详情	详情
(IV)	13572	N-[1-((2R,3R,4R,5R)-3,4-Bis[[tert-butyl(dimethyl)silyl]oxy]-5-methyltetrahydro-2-furanyl)-5-fluoro-2-oxo-1,2-dihydro-4-pyrimidinyl]-3,4,5-trimethoxybenzamide		C₃₁H₅₀FN₃O₈Si₂	详情	详情

Extended Information