[(2S,4S,5R)-5-(6-amino-9H-purin-9-yl)-4-fluorotetrahydro-2-furanyl]methyl acetate -Drug Synthesis Database

【结构式】

【分子编号】17632

【品名】[(2S,4S,5R)-5-(6-amino-9H-purin-9-yl)-4-fluorotetrahydro-2-furanyl]methyl acetate

【CA登记号】

【分子式】C₁₂H₁₄FN₅O₃

【分子量】295.2734632

【元素组成】C 48.81% H 4.78% F 6.43% N 23.72% O 16.26%

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：(XXI)

The regioseletive deacetylation of 9-(2,5-diacetoxy-3-bromo-3-deoxy-beta-D-xylofuranosyl)adenine (XVIII) by means of beta-cyclodextrin/NaHCO3 in water or hydrazine monohydrate in ethanol gives 9-(5-acetoxy-3-bromo-3-deoxy-beta-D-xylofuranosyl)adenine (XIX), which is debrominated by hydrogenation over Pd/C in acetonitrile/water, affording 9-(5-acetoxy-3-deoxy-beta-D-xylofuranosyl)adenine (XX). Finally, this compound is fluorinated by means of diethylamido sulfur trifluoride in refluxing dichloromethane, yielding (XXI) and deacetylated with NH3 to the target compound.

参考文献中间体

合成目标

【1】 Tanaka, Y.; Uchida, Y.; Shiragami, H.; Yukawa, T.; Iwagami, H.; Izawa, K.; A novel method for the synthesis of ddA and F-ddA via regioselective 2'-O-deacetylation of 9-(2, 5-di-O-acetyl-3-bromo-3-deoxy-beta-D-xylofuranosyl)adenine. Nucleosides Nucleotides 1992, 1, 391-400.
【2】 Castaner, J.; Graul, A.; Silvestre, J.S.; Lodenosine. Drugs Fut 1998, 23, 11, 1176-1189.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(XVIII)	17629	[(2R,3S,4S,5R)-4-(acetoxy)-5-(6-amino-9H-purin-9-yl)-3-bromotetrahydro-2-furanyl]methyl acetate	C₁₄H₁₆BrN₅O₅	详情	详情
(XIX)	17630	[(2R,3R,4S,5R)-5-(6-amino-9H-purin-9-yl)-3-bromo-4-hydroxytetrahydro-2-furanyl]methyl acetate	C₁₂H₁₄BrN₅O₄	详情	详情
(XX)	17631	[(2S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxytetrahydro-2-furanyl]methyl acetate	C₁₂H₁₅N₅O₄	详情	详情
(XXI)	17632	[(2S,4S,5R)-5-(6-amino-9H-purin-9-yl)-4-fluorotetrahydro-2-furanyl]methyl acetate	C₁₂H₁₄FN₅O₃	详情	详情

Extended Information