4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-5-fluoro-2(1H)-pyrimidinone -Drug Synthesis Database

【结构式】

【分子编号】58283

【品名】4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-5-fluoro-2(1H)-pyrimidinone

【CA登记号】

【分子式】C₉H₁₂FN₃O₅

【分子量】261.2099032

【元素组成】C 41.38% H 4.63% F 7.27% N 16.09% O 30.63%

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：(I)

The bromoacetylation of 5-fluorocytidine (I) with 2-acetoxyisobutyryl bromide (II) in acetonitrile, ethyl acetate or dichloromethane gives a mixture of two bromoacylated compounds (III) and (IV), with minor amounts of two other compounds (V) and (VI) that are separated by chromatography. The mixture of (III) and (IV), without separation, is treated with Zn/Cu in DMF or methanol/ethyl acetate to yield the unsaturated cytidine derivative (VII), which is finally deacylated by means of Na-OMe in methanol to afford the target fluorocytidine derivative.

参考文献中间体

合成目标

【1】 Confalone, P.N.; Jin, F. (Pharmasset, Inc.); Method for the synthesis of 2',3'-dideoxy-2',3'-didehydronucleosides. WO 0270533 .

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)	58283	4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-5-fluoro-2(1H)-pyrimidinone		C₉H₁₂FN₃O₅	详情	详情
(II)	12806	2-bromo-1,1-dimethyl-2-oxoethyl acetate; alpha-Acetoxy-isobutyryl bromide	40635-67-4	C₆H₉BrO₃	详情	详情
(III)	58284	{(2R,3R,5R)-3-(acetyloxy)-5-[4-amino-5-fluoro-2-oxo-1(2H)-pyrimidinyl]-4-bromotetrahydro-2-furanyl}methyl 2-(acetyloxy)-2-methylpropanoate		C₁₇H₂₁BrFN₃O₈	详情	详情
(IV)	58285	{(2R,4S,5R)-4-(acetyloxy)-5-[4-amino-5-fluoro-2-oxo-1(2H)-pyrimidinyl]-3-bromotetrahydro-2-furanyl}methyl 2-(acetyloxy)-2-methylpropanoate		C₁₇H₂₁BrFN₃O₈	详情	详情
(V)	58286	{(2R,3R,5R)-3-(acetyloxy)-5-[4-amino-5-fluoro-2-oxo-1(2H)-pyrimidinyl]-4-bromotetrahydro-2-furanyl}methyl acetate		C₁₃H₁₅BrFN₃O₆	详情	详情
(VI)	58287	{(2R,5R)-4-(acetyloxy)-5-[4-amino-5-fluoro-2-oxo-1(2H)-pyrimidinyl]-3-bromotetrahydro-2-furanyl}methyl acetate		C₁₃H₁₅BrFN₃O₆	详情	详情
(VII)	58288	{(2S,5R)-5-[4-amino-5-fluoro-2-oxo-1(2H)-pyrimidinyl]-2,5-dihydro-2-furanyl}methyl 2-(acetyloxy)-2-methylpropanoate		C₁₅H₁₈FN₃O₆	详情	详情

Extended Information