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【结 构 式】 
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【分子编号】56871 【品名】(2R,3R,4S,5R)-2-[(benzoyloxy)methyl]-5-bromo-4-fluorotetrahydro-3-furanyl benzoate 【CA登记号】 |
【 分 子 式 】C19H16BrFO5 【 分 子 量 】423.2354432 【元素组成】C 53.92% H 3.81% Br 18.88% F 4.49% O 18.9% |
合成路线1
该中间体在本合成路线中的序号：(III)The reaction of 1,3,5-tri-O-benzoyl-2-O-(trifluoromethanesulfonyl)-alpha-D-ribofuranose (I) with labeled tetrabutylammonium fluoride in acetonitrile gives 1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-alpha-D-arabinofuranose (II), which is treated with HBr/HOAc in dichloroethane to yield 3,5-di-O-benzoyl-2-deoxy-2-fluoro-alpha-D-arabinofuranosyl bromide (III). The condensation of (III) with thymine bis trimethylsilyl ether (IV) in dichloroethane affords a mixture of protected nucleoside alpha and beta anomers (V) and (VI), which, without separation, is deprotected with NaOMe in methanol and submitted to HPLC chromatographic separation to provide the target unprotected and labeled beta anomer.
| 【1】 Alauddin, M.M.; et al.; Synthesis of [18F]-labeled 2'-deoxy-2'-fluoro-5-methyl-1-beta-D-arabinofuranosyluracil ([18F]-FMAU). J Label Compd Radiopharm 2002, 45, 7, 583. |
| 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) | 56869 | (2R,3R,4R,5R)-4-(benzoyloxy)-5-[(benzoyloxy)methyl]-3-{[(trifluoromethyl)sulfonyl]oxy}tetrahydro-2-furanyl benzoate | C27H21F3O10S | 详情 | 详情 | |
| (II) | 17698 | [(2R,3R,4S,5R)-3,5-bis(benzoyloxy)-4-fluorotetrahydro-2-furanyl]methyl benzoate | C26H21FO7 | 详情 | 详情 | |
| (II) | 56870 | (2R,3S,4R,5R)-4-(benzoyloxy)-5-[(benzoyloxy)methyl]-3-fluorotetrahydro-2-furanyl benzoate | C26H21FO7 | 详情 | 详情 | |
| (III) | 17524 | [(2S,3S,4R,5S)-3-(benzoyloxy)-5-bromo-4-fluorotetrahydro-2-furanyl]methyl benzoate | C19H16BrFO5 | 详情 | 详情 | |
| (III) | 56871 | (2R,3R,4S,5R)-2-[(benzoyloxy)methyl]-5-bromo-4-fluorotetrahydro-3-furanyl benzoate | C19H16BrFO5 | 详情 | 详情 | |
| (IV) | 41900 | 5-methyl-2,4-bis[(trimethylsilyl)oxy]pyrimidine; 5-methyl-2-[(trimethylsilyl)oxy]-4-pyrimidinyl trimethylsilyl ether | 7288-28-0 | C11H22N2O2Si2 | 详情 | 详情 |
| (V) | 56872 | (2R,3R,4S,5S)-2-[(benzoyloxy)methyl]-4-fluoro-5-[5-methyl-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]tetrahydro-3-furanyl benzoate | C24H21FN2O7 | 详情 | 详情 | |
| (V) | 56874 | (2R,3R,4S,5S)-2-[(benzoyloxy)methyl]-4-fluoro-5-[5-methyl-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]tetrahydro-3-furanyl benzoate | C24H21FN2O7 | 详情 | 详情 | |
| (VI) | 56873 | (2R,3R,4S,5R)-2-[(benzoyloxy)methyl]-4-fluoro-5-[5-methyl-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]tetrahydro-3-furanyl benzoate | C24H21FN2O7 | 详情 | 详情 | |
| (VI) | 56875 | (2R,3R,4S,5R)-2-[(benzoyloxy)methyl]-4-fluoro-5-[5-methyl-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]tetrahydro-3-furanyl benzoate | C24H21FN2O7 | 详情 | 详情 |