N-[9-[(1R,4S)-4-(hydroxymethyl)-2-cyclopenten-1-yl]-6-oxo-6,9-dihydro-1H-purin-2-yl]acetamide -Drug Synthesis Database

【结构式】

【分子编号】45389

【品名】N-[9-[(1R,4S)-4-(hydroxymethyl)-2-cyclopenten-1-yl]-6-oxo-6,9-dihydro-1H-purin-2-yl]acetamide

【CA登记号】

【分子式】C₁₃H₁₅N₅O₃

【分子量】289.294

【元素组成】C 53.97% H 5.23% N 24.21% O 16.59%

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：(IX)

The reaction of the chiral epoxy-alcohol (I) with MsCl, TEA and DMAP gives the mesylate (II), which is treated with TBAF in THF to yield the unsaturated epoxide (III).The condensation of (III) with diaminopurine (IV) by means of NaH in DMF affords the carbocyclic purine (V), which is dehydroxylated by reaction with phenyl chlorothioformate, followed by a thermal elimination reaction with Bu3SnH and AIBN to provide the carbocyclic purine (VI). The debenzylation of (VI) by means of BF3/Et2O and Ac2O gives the diacetyl derivative (VII), which is selectively O-deacetylated with NH3 in methanol, yielding 2-acetamido-6-aminopurine (VIII). The reaction of (VIII) with NaNO2 and acetic acid affords the N-acetylated guanine derivative (IX), which is finally treated with NH3 in methanol to provide the target compound.

参考文献中间体

合成目标

【1】 Jones, M.F.; et al.; Total synthesis of (-)-carbovir. J Chem Soc - Perkins Trans I 1991, 10, 2479.

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)	29889	(1S,2R,3S,5R)-2-[(benzyloxy)methyl]-6-oxabicyclo[3.1.0]hexan-3-ol		C₁₃H₁₆O₃	详情	详情
(II)	45390	benzyl ((1S,2S,3S,5R)-3-[[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]-6-oxabicyclo[3.1.0]hex-2-yl)methyl ether; (1S,2S,3S,5R)-2-[(benzyloxy)methyl]-3-[[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]-6-oxabicyclo[3.1.0]hexane		C₁₆H₂₂O₃S	详情	详情
(III)	45384	benzyl (1S,2S,5R)-6-oxabicyclo[3.1.0]hex-3-en-2-ylmethyl ether; (1R,4S,5S)-4-[(benzyloxy)methyl]-6-oxabicyclo[3.1.0]hex-2-ene		C₁₃H₁₄O₂	详情	详情
(IV)	11644	6-Chloro-9H-purin-2-amine; 6-Chloro-9H-purin-2-ylamine; 2-Amino-6-chloropurine	10310-21-1	C₅H₄ClN₅	详情	详情
(V)	45385	(1S,2S,5S)-2-[(benzyloxy)methyl]-5-(2,6-diamino-9H-purin-9-yl)-3-cyclopenten-1-ol		C₁₈H₂₀N₆O₂	详情	详情
(VI)	45386	2-amino-9-[(1R,4S)-4-[(benzyloxy)methyl]-2-cyclopenten-1-yl]-9H-purin-6-ylamine; 9-[(1R,4S)-4-[(benzyloxy)methyl]-2-cyclopenten-1-yl]-9H-purine-2,6-diamine		C₁₈H₂₀N₆O	详情	详情
(VII)	45387	[(1S,4R)-4-[2-(acetamido)-6-amino-9H-purin-9-yl]-2-cyclopenten-1-yl]methyl acetate		C₁₅H₁₈N₆O₃	详情	详情
(VIII)	45388	N-[6-amino-9-[(1R,4S)-4-(hydroxymethyl)-2-cyclopenten-1-yl]-9H-purin-2-yl]acetamide		C₁₃H₁₆N₆O₂	详情	详情
(IX)	45389	N-[9-[(1R,4S)-4-(hydroxymethyl)-2-cyclopenten-1-yl]-6-oxo-6,9-dihydro-1H-purin-2-yl]acetamide		C₁₃H₁₅N₅O₃	详情	详情

Extended Information