[(2R,3R,4S,5R)-3-(benzoyloxy)-5-bromo-4-fluorotetrahydro-2-furanyl]methyl benzoate -Drug Synthesis Database

【结构式】

【分子编号】17705

【品名】[(2R,3R,4S,5R)-3-(benzoyloxy)-5-bromo-4-fluorotetrahydro-2-furanyl]methyl 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%

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：(XXII)

The controlled reaction of 1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-alpha-D-arabinofuranose (XI) with HBr in acetic acid gives the bromosugar (XXII), which is condensed with 6-chloropurine (V) as before, yielding 6-chloro-9-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-beta-D-arabinofuranosyl)purine (XXIII). Finally, this compound is treated with ammonia in methanol as before to afford intermediate 9-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)adenine (VII).

参考文献中间体

合成目标

【1】 Castaner, J.; Graul, A.; Silvestre, J.S.; Lodenosine. Drugs Fut 1998, 23, 11, 1176-1189.
【2】 Marquez, V.E.; Design, synthesis, and antiviral activity of nucleoside and nucleotide analogs. ACS Symp Ser 1989, 401, 140-55.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(V)	17692	6-Chloropurine; 6-chloro-9H-purine	87-42-3	C₅H₃ClN₄	详情	详情
(VII)	17694	(2R,3R,4S,5R)-5-(6-amino-9H-purin-9-yl)-4-fluoro-2-(hydroxymethyl)tetrahydro-3-furanol		C₁₀H₁₂FN₅O₃	详情	详情
(XI)	17698	[(2R,3R,4S,5R)-3,5-bis(benzoyloxy)-4-fluorotetrahydro-2-furanyl]methyl benzoate		C₂₆H₂₁FO₇	详情	详情
(XXII)	17705	[(2R,3R,4S,5R)-3-(benzoyloxy)-5-bromo-4-fluorotetrahydro-2-furanyl]methyl benzoate		C₁₉H₁₆BrFO₅	详情	详情
(XXIII)	17706	[(2R,3R,4S,5R)-3-(benzoyloxy)-5-(6-chloro-9H-purin-9-yl)-4-fluorotetrahydro-2-furanyl]methyl benzoate		C₂₄H₁₈ClFN₄O₅	详情	详情

Extended Information