[(3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2-ethoxy-2-methyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]methanol -Drug Synthesis Database

【结构式】

【分子编号】49214

【品名】[(3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2-ethoxy-2-methyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]methanol

【CA登记号】

【分子式】C₁₄H₁₉N₅O₅

【分子量】337.33556

【元素组成】C 49.85% H 5.68% N 20.76% O 23.71%

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：(III)

The reaction of adenosine (I) with triethyl orthoacetate (II) by means of Ts-OH in acetonitrile gives the bicyclic dioxolane (III), which is treated with acetyl bromide in dichloroethane to yield the acetylated bromonucleoside (IV). The debromination of (IV) by means of Bu3SnH in toluene affords the acetylated target compound (V), which is finally deprotected with ammonia in methanol.

参考文献中间体

合成目标

【1】 Norman, D.G.; Reese, C.B.; A convenient preparation of 3'-deoxyadenosine. Synthesis 1983, 304.

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)	11988	Adenosine; (2R,3R,4S,5R)-2-(6-Amino-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydro-3,4-furandiol	58-61-7	C₁₀H₁₃N₅O₄	详情	详情
(II)	12940	1,1-Diethoxyethyl ethyl ether; 1,1,1-Triethoxyethane; Triethyl orthoacetate	78-39-7	C₈H₁₈O₃	详情	详情
(III)	49214	[(3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2-ethoxy-2-methyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]methanol		C₁₄H₁₉N₅O₅	详情	详情
(IV)	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
(V)	49215	[(2S,4R,5R)-4-(acetoxy)-5-(6-amino-9H-purin-9-yl)tetrahydro-2-furanyl]methyl acetate		C₁₄H₁₇N₅O₅	详情	详情

Extended Information