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【结 构 式】

【分子编号】14419

【品名】tert-butyl(dimethyl)silyl [(1S,2S)-2-([[tert-butyl(dimethyl)silyl]oxy]methyl)-3,3-bis(methylsulfanyl)cyclobutyl]methyl ether; tert-butyl[[(1S,4S)-4-([[tert-butyl(dimethyl)silyl]oxy]methyl)-2,2-bis(methylsulfanyl)cyclobutyl]methoxy]dimethylsilane

【CA登记号】

【 分 子 式 】C20H44O2S2Si2

【 分 子 量 】436.87116

【元素组成】C 54.99% H 10.15% O 7.32% S 14.68% Si 12.86%

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:(IL)

6) The stereoselective cyclization of bis[(-)-menthyl] fumarate (XLVII) with 1,1-bis(methylsulfanyl)ethylene (XX) by means of diisobutylaluminum chloride in hexane gives (1S-trans)-3,3-bis(methylsulfanyl)cyclobutane-1,2-dicarboxylic acid di-(-)-menthyl ester (XLVIII), which is reduced with LiAlH4 in THF yielding (1S-trans)-3,3-bis(methylsulfanyl)cyclobutane-1,2-dimethanol (XXIV). The silylation of (XXIV) with tert-butyldimethylsilyl chloride (TBMS-Cl) and imidazole in DMF affords the bis-silylated diol (II), which is treated with AgNO3 and N-chlorosuccinimide (NCS) in acetonitrile/water to give the cyclobutanone (L). The reaction of (L) with O-methylhydroxylamine in pyridine yields the corresponding O-methyloxime (LI), which is selectively reduced with NaBH4 in THF to the cyclobutylamine (LII). The condensation of (LII) with 4-chloro-6-hydroxy-5-nitropyrimidine-2-amine (LIII) by means of triethylamine in DMF affords the substituted 5-nitro-2,4-diaminopyrimidine (LIV), which is reduced with H2 over Pd/C in formic acid yielding the corresponding triaminopyrimidine (LV). Finally, this compound, without isolation, is cyclized with formic acid at 130 C.

1 Ireland, C.; Leeson, P.A.; Castaner, J.; Lobucavir. Drugs Fut 1997, 22, 4, 359.
2 Pariza, R.J.; Hannick, S.M.; Sowin, T.J.; Doherty, E.M. (Bristol-Myers Squibb Co.); Process for preparing substd. Cyclobutanes. US 5399775 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(IL) 14419 tert-butyl(dimethyl)silyl [(1S,2S)-2-([[tert-butyl(dimethyl)silyl]oxy]methyl)-3,3-bis(methylsulfanyl)cyclobutyl]methyl ether; tert-butyl[[(1S,4S)-4-([[tert-butyl(dimethyl)silyl]oxy]methyl)-2,2-bis(methylsulfanyl)cyclobutyl]methoxy]dimethylsilane C20H44O2S2Si2 详情 详情
(XLVII) 14417 bis[(1R,2S,4S)-2-isopropyl-4-methylcyclohexyl] (E)-2-butenedioate C24H40O4 详情 详情
(XLVIII) 14418 bis[(1R,2S,4S)-2-isopropyl-4-methylcyclohexyl] (1S,2S)-3,3-bis(methylsulfanyl)-1,2-cyclobutanedicarboxylate C28H48O4S2 详情 详情
(L) 14420 (2S,3S)-2,3-bis([[tert-butyl(dimethyl)silyl]oxy]methyl)cyclobutanone C18H38O3Si2 详情 详情
(LI) 14421 (2R,3S)-2,3-bis([[tert-butyl(dimethyl)silyl]oxy]methyl)cyclobutanone O-methyloxime C19H41NO3Si2 详情 详情
(LII) 14422 (1R,2R,3S)-2,3-bis([[tert-butyl(dimethyl)silyl]oxy]methyl)cyclobutanamine; (1R,2R,3S)-2,3-bis([[tert-butyl(dimethyl)silyl]oxy]methyl)cyclobutylamine C18H41NO2Si2 详情 详情
(LIII) 14423 2-amino-6-chloro-5-nitro-4-pyrimidinol C4H3ClN4O3 详情 详情
(LIV) 14424 2-amino-6-[[(1R,2R,3S)-2,3-bis([[tert-butyl(dimethyl)silyl]oxy]methyl)cyclobutyl]amino]-5-nitro-4-pyrimidinol C22H43N5O5Si2 详情 详情
(LV) 14425 2,5-diamino-6-[[(1R,2R,3S)-2,3-bis(hydroxymethyl)cyclobutyl]amino]-4-pyrimidinol C10H17N5O3 详情 详情
Extended Information