2-(acetamido)-9H-purin-6-yl diphenylcarbamate -Drug Synthesis Database

【结构式】

【分子编号】37775

【品名】2-(acetamido)-9H-purin-6-yl diphenylcarbamate

【CA登记号】

【分子式】C₂₀H₁₆N₆O₃

【分子量】388.38568

【元素组成】C 61.85% H 4.15% N 21.64% O 12.36%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(I)

The enantiocontrolled condensation of the protected guanine (I) with cis-1,3-bis(benzoyloxy)-4-cyclopentene (II) catalyzed by a chiral Pd catalyst gives the alkylated guanine (III), which is condensed with the nitrosulfone (IV) by means of PPh3 and TEA to yield the intermediate (V). The oxidation of (V) with oxone, tetramethylguanidine, and Na2CO3 in methanol/dichloromethane affords the cyclopentenecarboxylate (VI), which is finally reduced with calcium borohydride and deprotected with ammonia to provide the target compound.

参考文献中间体

合成目标

【1】 Madsen, R.; Brown, B.; Guile, S.D.; Trost, B.M.; Palladium-catalyzed enantioselective synthesis of carbanucleosides. J Am Chem Soc 2000, 122, 25, 5947.

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)	37775	2-(acetamido)-9H-purin-6-yl diphenylcarbamate		C₂₀H₁₆N₆O₃	详情	详情
(II)	37776	(1R,4S)-4-(benzoyloxy)-2-cyclopenten-1-yl benzoate		C₁₉H₁₆O₄	详情	详情
(III)	37777	(1S,4R)-4-(2-(acetamido)-6-[[(diphenylamino)carbonyl]oxy]-9H-purin-9-yl)-2-cyclopenten-1-yl benzoate		C₃₂H₂₆N₆O₅	详情	详情
(IV)	37778	(nitromethyl)(dioxo)phenyl-lambda(6)-sulfane; nitromethyl phenyl sulfone	21272-85-5	C₇H₇NO₄S	详情	详情
(V)	37779	2-(acetamido)-9-[(1R,4S)-4-[(S)-nitro(phenylsulfonyl)methyl]-2-cyclopenten-1-yl]-9H-purin-6-yl diphenylcarbamate		C₃₂H₂₇N₇O₇S	详情	详情
(VI)	37780	methyl (1S,4R)-4-(2-(acetamido)-6-[[(diphenylamino)carbonyl]oxy]-9H-purin-9-yl)-2-cyclopentene-1-carboxylate		C₂₇H₂₄N₆O₅	详情	详情

合成路线2

该中间体在本合成路线中的序号：(XLII)

Yet another method was based on the alkylation of 2-N-acetyl-6-O-diphenylcarbamoylguanine (XLII) with tosylate (XXII) to give (XLIII). This was hydrolyzed to the precursor (XXV) by treatment with KOH.

参考文献中间体

合成目标

【1】 Synthesis of acyclic nucleoside derivs.. WO 0008025 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(XXII)	52971	(2S)-4,4-diethoxy-2-({[(4-methylphenyl)sulfonyl]oxy}methyl)butyl acetate		C₁₈H₂₈O₇S	详情	详情
(XXV)	52974	2-amino-9-[(2R)-4,4-diethoxy-2-(hydroxymethyl)butyl]-1,9-dihydro-6H-purin-6-one		C₁₄H₂₃N₅O₄	详情	详情
(XLII)	37775	2-(acetamido)-9H-purin-6-yl diphenylcarbamate		C₂₀H₁₆N₆O₃	详情	详情
(XLIII)	52988	(2R)-2-[(2-(acetylamino)-6-{[(diphenylamino)carbonyl]oxy}-9H-purin-9-yl)methyl]-4,4-diethoxybutyl acetate	n/a	C₃₁H₃₆N₆O₇	详情	详情

Extended Information