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【结 构 式】

【分子编号】56873

【品名】(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

【CA登记号】

【 分 子 式 】C24H21FN2O7

【 分 子 量 】468.4384232

【元素组成】C 61.54% H 4.52% F 4.06% N 5.98% O 23.91%

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:(VI)

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
Extended Information