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【结 构 式】

【分子编号】58285

【品名】{(2R,4S,5R)-4-(acetyloxy)-5-[4-amino-5-fluoro-2-oxo-1(2H)-pyrimidinyl]-3-bromotetrahydro-2-furanyl}methyl 2-(acetyloxy)-2-methylpropanoate

【CA登记号】

【 分 子 式 】C17H21BrFN3O8

【 分 子 量 】494.2715632

【元素组成】C 41.31% H 4.28% Br 16.17% F 3.84% N 8.5% O 25.9%

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:(IV)

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.

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
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