(2R,3S,4R,5R)-2-(6-amino-9H-purin-9-yl)-4-bromo-5-(hydroxymethyl)tetrahydro-3-furanol -Drug Synthesis Database

【结构式】

【分子编号】49216

【品名】(2R,3S,4R,5R)-2-(6-amino-9H-purin-9-yl)-4-bromo-5-(hydroxymethyl)tetrahydro-3-furanol

【CA登记号】

【分子式】C₁₀H₁₂BrN₅O₃

【分子量】330.14118

【元素组成】C 36.38% H 3.66% Br 24.2% N 21.21% O 14.54%

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：(V)

The reaction of adenosine (I) with 2-acetoxyisobutyryl bromide (A) gives the 3'-bromonucleoside (II) along with some 3'-bromo regioisomer (III). The reaction of the desired isomer (II) with HCl in methanol yields the intermediate acetylated 3'-bromonucleoside (V) and finally the 3'-bromo-3'-deoxyadenosine (VI). This compound is then debrominated by hydrogenation with H2 over Pd/C in ethanol/water.

参考文献中间体

合成目标

【1】 Aman, S.; et al.; From adenosine to 3'-deoxyadenosine: Development and scale up. Org Process Res Dev 2000, 4, 6, 601.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(A)	49211	1-(bromocarbonyl)-2-methylpropyl acetate		C₇H₁₁BrO₃	详情	详情
(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)	49212	(2R,3S,4S,5R)-2-(6-amino-9H-purin-9-yl)-4-bromo-5-[[(2,4,4-trimethyl-5-oxo-1,3-dioxolan-2-yl)oxy]methyl]tetrahydro-3-furanyl acetate		C₁₈H₂₂BrN₅O₇	详情	详情
(III)	36390	(2R,3R,4S,5R)-5-(6-amino-9H-purin-9-yl)-4-bromo-2-[[(2,4,4-trimethyl-5-oxo-1,3-dioxolan-2-yl)oxy]methyl]tetrahydro-3-furanyl acetate		C₁₈H₂₂BrN₅O₇	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)	49216	(2R,3S,4R,5R)-2-(6-amino-9H-purin-9-yl)-4-bromo-5-(hydroxymethyl)tetrahydro-3-furanol		C₁₀H₁₂BrN₅O₃	详情	详情

Extended Information