(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 -Drug Synthesis Database

【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.

参考文献中间体

合成目标

【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