[(1S,2R,4R,5R)-4-(6-amino-9H-purin-9-yl)-3,6-dioxabicyclo[3.1.0]hex-2-yl]methanol -Drug Synthesis Database

【结构式】

【分子编号】49213

【品名】[(1S,2R,4R,5R)-4-(6-amino-9H-purin-9-yl)-3,6-dioxabicyclo[3.1.0]hex-2-yl]methanol

【CA登记号】

【分子式】C₁₀H₁₁N₅O₃

【分子量】249.22924

【元素组成】C 48.19% H 4.45% N 28.1% O 19.26%

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) 2-acetoxyisobutyryl bromide (A) in acetonitrile/water gives a mixture of the 3-bromo (II) and 2-bromo nucleosides (III), which is treated with Dowex (OH), Amberlite (OH) or methanolic NaOMe to yield the epoxide (IV). Finally, this compound is reduced with LiEt3BH in THF/DMSO or LiAlH4 in THF to afford a mixture of the 2'-deoxy nucleoside (V) and the target compound that are separated by chromatography. Alternatively, the mixture of the nucleosides (II) and (III) is debrominated by reaction with Bu3SnH and AIBN in refluxing toluene to give the same mixture of (V) and the target compound that is separated as before.

参考文献中间体

合成目标

【1】 Russell, A.F.; et al.; Reactions of 2-acyloxyisobutyryl halides with nucleosides. II. Reactions of adenosine. J Am Chem Soc 1973, 95, 12, 4025.
【2】 Hansske, F.; Robins, M.J.; Regiospecific and stereoselective conversion of ribonucleosides to 3'-deoxynucleosides. A high yield three-stage synthesis of cordycepin from adenosine. Tetrahedron Lett 1985, 26, 36, 4295.
【3】 Bazin, H.; Chattopadhyaya, J.; A convenient preparation of 3'-deoxyadenosine (cordycepin) and 9-[3'(R)-deuterio-beta-D-2'(R)-pentofuranosyl]-adenine. Synthesis 1985, 1108.
【4】 Robins, M.J.; et al.; Nucleic acid related compounds. 88. Efficient conversions of ribonucleosides into their 2',3'-anhydro, 2'(and 3')-deoxy, 2',3'-didehydro-2',3'-dideoxy, and 2',3'-dideoxynucleoside analogues. J Org Chem 1995, 60, 24, 7902.

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)	48061	1-[3-(2,3-dihydro-1H-inden-5-yloxy)-2-[(2-methoxyethoxy)methyl]-3-oxopropyl]cyclopentanecarboxylic acid		C₂₂H₃₀O₆	详情	详情
(V)	49213	[(1S,2R,4R,5R)-4-(6-amino-9H-purin-9-yl)-3,6-dioxabicyclo[3.1.0]hex-2-yl]methanol		C₁₀H₁₁N₅O₃	详情	详情

Extended Information