[(2S,5R)-5-(2-amino-6-chloro-9H-purin-9-yl)-2,5-dihydro-2-furanyl]methanol -Drug Synthesis Database

【结构式】

【分子编号】55892

【品名】[(2S,5R)-5-(2-amino-6-chloro-9H-purin-9-yl)-2,5-dihydro-2-furanyl]methanol

【CA登记号】

【分子式】C₁₀H₁₀ClN₅O₂

【分子量】267.6746

【元素组成】C 44.87% H 3.77% Cl 13.24% N 26.16% O 11.95%

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)

Treatment of 2-amino-6-chloro-9-beta-D-ribofuranosylpurine (I) with acetoxyisobutyryl bromide (II) led to a mixture of acetoxy bromo derivatives (III) and (IV) which, upon reductive treatment with activated zinc, furnished the 2',3'-dehydro compound (V). Deprotection of (V) with K2CO3 in aqueous methanol provided the free nucleoside (VI). Finally, nucleophilic displacement of the chlorine of (VI) with cyclopropylamine (VII) afforded the target compound.

参考文献中间体

合成目标

【1】 Chu, C.K.; Ray, A.S.; Anderson, K.S.; Yang, Z.; Novel use of a guanosine prodrug approach to convert 2',3'-didehydro-2',3'-dideoxyguanosine into a viable antiviral agent. Antimicrob Agents Chemother 2002, 46, 3, 887.

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)	55888	(2R,3S,4R,5R)-2-(2-amino-6-chloro-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydro-3,4-furandiol		C₁₀H₁₂ClN₅O₄	详情	详情
(II)	12806	2-bromo-1,1-dimethyl-2-oxoethyl acetate; alpha-Acetoxy-isobutyryl bromide	40635-67-4	C₆H₉BrO₃	详情	详情
(III)	55889	(2R,5R)-2-(2-amino-6-chloro-9H-purin-9-yl)-4-bromo-5-{[(2,4,4-trimethyl-5-oxo-1,3-dioxolan-2-yl)oxy]methyl}tetrahydro-3-furanyl acetate		C₁₈H₂₁BrClN₅O₇	详情	详情
(IV)	55890	(2R,5R)-5-(2-amino-6-chloro-9H-purin-9-yl)-4-bromo-2-{[(2,4,4-trimethyl-5-oxo-1,3-dioxolan-2-yl)oxy]methyl}tetrahydro-3-furanyl acetate		C₁₈H₂₁BrClN₅O₇	详情	详情
(V)	55891	2-{[(2S,5R)-5-(2-amino-6-chloro-9H-purin-9-yl)-2,5-dihydro-2-furanyl]methoxy}-2,5,5-trimethyl-1,3-dioxolan-4-one		C₁₆H₁₈ClN₅O₅	详情	详情
(VI)	55892	[(2S,5R)-5-(2-amino-6-chloro-9H-purin-9-yl)-2,5-dihydro-2-furanyl]methanol		C₁₀H₁₀ClN₅O₂	详情	详情
(VII)	12263	Cyclopropylamine; Cyclopropanamine	765-30-0	C₃H₇N	详情	详情

Extended Information