CAS: 651324-06-0; (3R,4R,5S)-Ethyl 4-(Tert-Butylamino)-5-(Diallylamino)-3-(Pentan-3-Yloxy)Cyclohex-1-Enecarboxylate
该化合物是一个复杂的有机化合物,具有独特的结构特征.该化合物含有一个环己烷环,有助于其循环和不饱和性质,以及一个含有酸性特性的碳箱酸功能组.多种氨基氨基化合物的存在表明氢联结和再活的潜力,而乙基乙基乙基酯的细胞表明它能够进行水解以释放相应的酸.该化合物的立体化学学学,以其独特的结构(3R,4R,5S)为标志,提出了能够影响其生物活动和互动的具体空间安排.此外,分种烷基化合物,如四丁基和乙基丙基氧基化合物组,可能加强其脂性,影响其溶性,但会的化合物或集化性,从而显示其具体的生物结构.
- 英文名称(3R,4R,5S)-Ethyl 4-(Tert-Butylamino)-5-(Diallylamino)-3-(Pentan-3-Yloxy)Cyclohex-1-Enecarboxylate
- 中文名称奥司他韦杂质21
- IUPAC名称ethyl (3R,4R,5S)-4-(tert-butylamino)-5-(diallylamino)-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate
- 其它别名Ethyl (3R,4R,5S)-5-[bis(Prop-2-Enyl)Amino]-4-(Tert-Butylamino)-3-Pentan-3-Yloxycyclohexene-1-Carboxylate; (1S,5R,6S)-Ethyl 5-(Pentan-2-Yloxy)-7-Oxabicyclo[4.1.0]Hept-3-Ene-3-Carboxylate; 1-Cyclohexene-1-Carboxylic Acid, 4-[(1,1-Dimethylethyl)Amino]-5-(Di-2-Propen-1-Ylamino)-3-(1-Ethylpropoxy)-, Ethyl Ester, (3R,4R,5S)-; (3R,4R,5S)-Ethyl 4-(Tert-Butylamino)-5-(Diallylamino)-3-(Pentan-3-Yloxy)Cyclohex-1-Enecarboxylate; Ethyl (3R,4R,5S)-4-(Tert-Butylamino)-5-(Diallylamino)-3-(Pentan-3-Yloxy)Cyclohex-1-Ene-1-Carboxylate; Oseltamivir?Impurity?59/ethyl?(3R,4R,5S)-4-(Tert-Butylamino)-5-(Diallylamino)-3-(Pentan-3-Yloxy)Cyclohex-1-Ene-1-Carboxylate; Ethyl (3R,4R,5S)-4-(Tert-Butylamino)-5-(Diallylamino)-3-(Pentan-3-Yloxy)Cyclohex-1-Ene-1-Carboxylate (Oseltamivir Impurity）; Ethyl (3R,4R,5S)-5-N,N-Diallylamino-4-(1,1-Dimethylethyl)Amino-3-(1-Ethylpropoxy)-1-Cyclohexene-1-Carboxylate
- CAS编号651324-06-0
- MFCD编号:MFCD30534110
- FDA UNII编号:45H3J6295Y
- 分子式:C24H42N2O3分子量:405.59
- 产品CID: 2533100
- 产品分类分析化学 → 标准品 → 药典标准品和杂质标准品
物理性质
上下游产品
diallylamine (1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester (3R,4S,5R)-[5-(tert-butylamino)-4-hydroxy-3-(pent-3-yloxy)]cyclohex-1-ene-1-carboxylic acid ethyl ester ethyl (3R,4S,5R)-4,5-(1,1-Dimethylethyl)imino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate ethyl (3R,4R,5S)-4-N-acetyl(1,1-dimethylethyl)amino-5-N,N-diallylamino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate oseltamivir oseltamivir phosphate合成工艺路线路线简述
📜5-(戊烷-3-基氧基)-7-氧代-双环[4.1.0]庚-3-烯-3-羧酸乙酯置于potassium Carbonate,三乙胺,苯磺酸,Magnesium Chloride体系中,用 甲苯 作为反应溶剂,化学反应 36.0H,反应生成 奥司他韦杂质21
参考文献:The Synthetic Development Of The Anti-Influenza Neuraminidase Inhibitor Oseltamivir Phosphate (Tamiflu®): A Challenge For Synthesis & Process Research
标题:The Synthetic Development Of The Anti-Influenza Neuraminidase Inhibitor Oseltamivir Phosphate (Tamiflu®): A Challenge For Synthesis & Process Research
摘要:该文描述了奥司他韦磷酸酯(tamiflu®)的合成演变历程,该药用于口服治疗和预防流感病毒感染(病毒性流感).奥司他韦磷酸酯是相应酸的乙酯酯前药,是一种强效且选择性的流感神经氨酸酶抑制剂.文中回顾了从(-)-樟脑酸经由合成非常好发展的环氧化合物基团和叠氮化反应到达奥司他韦磷酸酯的发现化学途径和可扩展途径,以及用于千克级实验室生产的技术途径.讨论了关于将关键环氧化合物基团转化为奥司他韦磷酸酯的无叠氮化反应的合成和工艺研究调查.为满足大规模生产需求,文中提出了独立于樟脑酸的奥司他韦磷酸新途径的探索,包括diels-Alder方法和利用非对称化概念对芳香环的转化.
DOI:10.2533/000942904777677605
海关参考信息
- 2901210000-乙烯
2901220000-丙烯
2905122000-异丙醇
2909110000-乙醚 - 💡 提示：海关信息按照顺序优先匹配，如需确认的海关信息，请参考相关资料。
- 详情请参考：📖 海关编码查询和海关进出口税则
专利信息
专利号:US-8304553-B2
优先权日:2007-12-19
标题:Method of forming oseltamivir and derivatives thereof
发明人：LIU XUEWEI; MA JIMEI
权利人:LIU XUEWEI; MA JIMEI; UNIV NANYANG TECH
摘要:A process is provided for the synthesis of 4,5-diamino cyclohexene carboxylate ester (1): or a pharmaceutically acceptable salt thereof. R 1 -R 3 are a silyl-, an aliphatic, alicyclic, aromatic, arylaliphatic, or an arylalicyclic group. R 4 , R 11 and R 12 are H, a silyl-group, an aliphatic, alicyclic, aromatic, arylaliphatic, or an arylalicyclic group. 3,4-Dihydropyran compound (9): with R 5 and R 6 being suitable protecting groups, is reacted to form aldehyde (4): which is oxidized and converted to N-substituted carbamate (3): with R 7 being a suitable protecting group. (3) is, via oxazolinidone (13): converted to azido carboxylate ester (2): and then to 4,5-diamino cyclohexene carboxylate ester (1).
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合成参考文献
摘要:Kleemann, A.; Engel, J.; Kutscher, B.; Reichert, D., Pharmaceutical Substances[Online], Thieme: Stuttgart, (2008).
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