CAS: 651324-04-8; (3R,4S,5R)-Ethyl 5-(Tert-Butylamino)-4-Hydroxy-3-(Pentan-3-Yloxy)Cyclohex-1-Enecarboxylate

该化合物是一个复杂的有机化合物,其特征是环己烷环状结构,有助于其反应性和稳定性.一个碳oxylic酸功能组的存在表明它可能在不同化学反应中具有酸性和再活性,而乙酯酸表明它可以进行水解以释放相应的酸.该化合物还具有氢氧基化合物的特征,可以参与氢结合,增强其在极溶溶剂中的溶性.该聚物组的成型叔丁基丁基氨基氨基化合物可能会影响该化合物的性能和生物活动,从而可能影响其与生物目标的相互作用.

英文名称(3R,4S,5R)-Ethyl 5-(Tert-Butylamino)-4-Hydroxy-3-(Pentan-3-Yloxy)Cyclohex-1-Enecarboxylate
中文名称奥司他韦杂质63
IUPAC名称ethyl (3R,4S,5R)-5-(tert-butylamino)-4-hydroxy-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate
其它别名Oseltamivir Impurity 48; Oseltamivir Impurity 63; (3R,4S,5R)-Ethyl 5-(Tert-Butylamino); 1-Cyclohexene-1-Carboxylic Acid, 5-[(1,1-Dimethylethyl)Amino]-3-(1-Ethylpropoxy)-4-Hydroxy-, Ethyl Ester, (3R,4S,5R)-; (3R,4S,5R)-Ethyl 5-(Tert-Butylamino)-4-Hydroxy-3-(Pentan-3-Yloxy)Cyclohex-1-Enecarboxylate; Ethyl (3R,4S,5R)-5-(Tert-Butylamino)-4-Hydroxy-3-(Pentan-3-Yloxy)Cyclohex-1-Ene-1-Carboxylate; Oseltamivir Impurity 57/ethyl (3R,4S,5R)-5-(Tert-Butylamino)-4-Hydroxy-3-(Pentan-3-Yloxy)Cyclohex-1-Ene-1-Carboxylate; Ethyl (3R,4S,5R)-5-(Tert-Butylamino)-4-Hydroxy-3-(Pentan-3-Yloxy)Cyclohex-1-Ene-1-Carboxylate (Oseltamivir Impurity)
CAS编号651324-04-8
MFCD编号:MFCD30534109
FDA UNII编号:9MY2932JH9
分子式:C18H33NO4分子量:327.46
产品CID: 2533102
产品分类分析化学 → 标准品 → 药典标准品和杂质标准品

相似结构搜索
InChIKey: QKBSLGDKUALQOQ-OAGGEKHMSA-N
InChI=1S/C18H33NO4/c1-7-13(8-2)23-15-11-12(17(21)22-9-3)10-14(16(15)20)19-18(4,5)6/h11,13-16,19-20H,7-10H2,1-6H3/t14-,15-,16+/m1/s1
计算化学: 氢键受体数5.0氢键供体数2.0可旋转键数9.0

MSDS等安全信息

警示词Warning
危险描述H302-H315-H319-H335-
防范说明P261-P305+P351+P338-
安全声明H303+H313+H333

上下游产品

tert-butylaminetert-butylamine (1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester (1S,5R,6R)-5-(1-ethyl-propoxy)-7-oxa-bicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester oseltamivir oseltamivir phosphate ethyl (3R,4R,5S)-4-N-acetyl(1,1-dimethylethyl)amino-5-N,N-diallylamino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate ethyl (3R,4R,5S)-5-N,N-diallylamino-4-(1,1-dimethylethyl)amino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate

合成工艺路线路线简述

📜叔丁胺,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magnesium Chloride,柠檬酸体系中,用甲苯作为反应溶剂,化学反应 23.0H,以91%的收率获得产物奥司他韦杂质63
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