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【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).

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