(2R,3S,4R,5R)-2-(hydroxymethyl)-5-{6-[(3R)tetrahydro-3-furanylamino]-9H-purin-9-yl}tetrahydro-3,4-furandiol -Drug Synthesis Database

【结构式】

【分子编号】53575

【品名】(2R,3S,4R,5R)-2-(hydroxymethyl)-5-{6-[(3R)tetrahydro-3-furanylamino]-9H-purin-9-yl}tetrahydro-3,4-furandiol

【CA登记号】n/a

【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 the chloropurine (I) with tetrahydrofuran-2(R)-amine (II) gives N6-(furan-2(R)-yl)adenosine (III), which is treated with 2,2-dimethoxypropane and Ts-OH in hot DMF to yield N6-(furan-2-(R)-yl)-2'O,3'O-isopropylideneadenosine (IV). The reaction of (IV) with CDI and methylamine in THF affords N6-(furan-2-(R)-yl)-2'O,3'O-isopropylidene-5'O-(N-methylcarbamoyl)adenosine (V), which is finally deprotected with HOAc in hot water to provide the target adenosine derivative.

参考文献中间体

合成目标

【1】 Palle, V.P.; et al.; A1 adenosine receptor agonist- SAR of 5'-carbamates and 5'-thionocarbamates of N6-substituted adenosine derivatives. 223rd ACS Natl Meet (April 7 2002, Orlando) 2002, Abst MEDI 23.
【2】 Belardinelli, L.; Zablocki, J.A.; Palle, V.P.; Ibrahim, P.N.; Varkhedkar, V. (CV Therapeutics, Inc.); N6 Heterocylic 5' modified adenosine derivs.. US 6258793; WO 0140244; WO 0140245 .

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)	18716	6-chloropurine riboside; (2R,3R,4S,5R)-2-(6-chloro-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydro-3,4-furandiol	2004-06-0	C₁₀H₁₁ClN₄O₄	详情	详情
(II)	53578	(3R)-tetrahydro-3-furanamine; (3R)-tetrahydro-3-furanylamine	n/a	C₄H₉NO	详情	详情
(III)	53575	(2R,3S,4R,5R)-2-(hydroxymethyl)-5-{6-[(3R)tetrahydro-3-furanylamino]-9H-purin-9-yl}tetrahydro-3,4-furandiol	n/a	C₁₄H₁₉N₅O₅	详情	详情
(IV)	53576	((3aR,4R,6R,6aS)-2,2-dimethyl-6-{6-[(3R)tetrahydro-3-furanylamino]-9H-purin-9-yl}tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol	n/a	C₁₇H₂₃N₅O₅	详情	详情
(V)	53577	((3aR,4R,6R,6aS)-2,2-dimethyl-6-{6-[(3R)tetrahydro-3-furanylamino]-9H-purin-9-yl}tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl methylcarbamate	n/a	C₁₉H₂₆N₆O₆	详情	详情

Extended Information