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

【结构式】

【分子编号】55508

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

【CA登记号】

【分子式】C₁₂H₁₂ClFN₄O₃

【分子量】314.7035432

【元素组成】C 45.8% H 3.84% Cl 11.27% F 6.04% N 17.8% O 15.25%

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 inosine (I) with trimethyl orthoacetate and HOAc, followed by a treatment with acetyl bromide, gives 3'-beta-bromo-3'-deoxyinosine (II), which is debrominated by means of Bu3SnH and AIBN in toluene to yield 3'-deoxyinosine (III). The reaction of (III) with SOCl2 /DMF in refluxing dichloromethane or with POCl3 /TEA in refluxing acetonitrile yields the 6-chloropurine (IV), which is regioselectively monodeacetylated with TEA in methanol to afford the hydroxy compound (V). The fluorination of (V) with morpholinosulfur trifluoride (MOST) and pyridine in dichloromethane gives the 3'-beta-fluoro derivative (VI), which is finally deprotected with ammonia in THF to provide the target lodenosine.

参考文献中间体

合成目标

【1】 Takamatsu, S.; et al.; 9-(2,3-Dideoxy-2-fluoro-beta-D-threo-pentofuranosyl)adenine (FddA) via a purine 3'-deoxynucleoside. J Org Chem 2001, 66, 22, 7469.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	38013	9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-1,9-dihydro-6H-purin-6-one	C₁₀H₁₂N₄O₅	详情	详情
(II)	55505	[(2R,3S,4S,5R)-4-(acetyloxy)-3-bromo-5-(6-oxo-1,6-dihydro-9H-purin-9-yl)tetrahydro-2-furanyl]methyl acetate	C₁₄H₁₅BrN₄O₆	详情	详情
(III)	55506	(2R,3R,5S)-5-[(acetyloxy)methyl]-2-(6-oxo-1,6-dihydro-9H-purin-9-yl)tetrahydro-3-furanyl acetate	C₁₄H₁₆N₄O₆	详情	详情
(IV)	55507	[(2S,4R,5R)-4-(acetyloxy)-5-(6-chloro-9H-purin-9-yl)tetrahydro-2-furanyl]methyl acetate	C₁₄H₁₅ClN₄O₅	详情	详情
(V)	55509	[(2S,4R,5R)-5-(6-chloro-9H-purin-9-yl)-4-hydroxytetrahydro-2-furanyl]methyl acetate	C₁₂H₁₃ClN₄O₄	详情	详情
(VI)	55508	[(2S,4S,5R)-5-(6-chloro-9H-purin-9-yl)-4-fluorotetrahydro-2-furanyl]methyl acetate	C₁₂H₁₂ClFN₄O₃	详情	详情

Extended Information