(1R)-1-[(4R,5R)-5-[(6-amino-9H-purin-9-yl)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-1,2-ethanediol -Drug Synthesis Database

【结构式】

【分子编号】17561

【品名】(1R)-1-[(4R,5R)-5-[(6-amino-9H-purin-9-yl)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-1,2-ethanediol

【CA登记号】

【分子式】C₁₃H₁₉N₅O₄

【分子量】309.32516

【元素组成】C 50.48% H 6.19% N 22.64% O 20.69%

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：(II)

A new synthesis of neplanocin A has been reported: The ring opening of 2',3'-O-isopropylideneadenine (I) with diisobutylaluminum hydride (DIBAL) in THF gives (2S,3R,4R)-9-[4,5-dihydroxy-2,3-(isopropylidenedioxy)pentyl]adenosine (II), which is partially protected with tert-butyldimethylsilyl chloride (TBDMS-Cl) and imidazole in DMF yielding the monosilylated compound (III). The Dess-Martin oxidation of (III) in dichloromethane affords the correponding ketone (IV), which is cyclized with the lithium derivative of the trimethylsilyl diazomethane in THF/hexane to give the proteced compound 2,3-O-isopropylidene-4'-O-(tert-butyldimethylsilyl)neplanocin A (V). Finally, this compound is deprotected by the usual deprotection methods.

参考文献中间体

合成目标

【1】 Niizuma, S.; Matsuda, A.; Shuto, S.; New neplanocin analogues. 10. The conversion of adenosine to neplanocin A, a carbocyclic nucleoside antibiotic with potent antiviral activity. Tetrahedron 1997, 53, 40, 13621.

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)	17560	[(3aR,4R,6R,6aS)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]methanol	362-75-4	C₁₃H₁₇N₅O₄	详情	详情
(II)	17561	(1R)-1-[(4R,5R)-5-[(6-amino-9H-purin-9-yl)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-1,2-ethanediol		C₁₃H₁₉N₅O₄	详情	详情
(III)	17562	(1R)-1-[(4R,5R)-5-[(6-amino-9H-purin-9-yl)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-2-[[tert-butyl(dimethyl)silyl]oxy]-1-ethanol		C₁₉H₃₃N₅O₄Si	详情	详情
(IV)	17563	1-[(4S,5R)-5-[(6-amino-9H-purin-9-yl)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-2-[[tert-butyl(dimethyl)silyl]oxy]-1-ethanone		C₁₉H₃₁N₅O₄Si	详情	详情
(V)	17564	9-[(3aR,4R,6aR)-6-([[tert-butyl(dimethyl)silyl]oxy]methyl)-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]-9H-purin-6-ylamine		C₂₀H₃₁N₅O₃Si	详情	详情

Extended Information