CAS: 956267-10-0; Ethyl (3R,4R,5S)-5-Acetamido-4-Amino-3-(Pentan-3-Yloxy)Cyclohex-1-Ene-1-Carboxylate

英文名称Ethyl (3R,4R,5S)-5-Acetamido-4-Amino-3-(Pentan-3-Yloxy)Cyclohex-1-Ene-1-Carboxylate
中文名称4-N-脱乙酰基-5-N-乙酰基奥塞米韦
IUPAC名称ethyl (3R,4R,5S)-5-acetamido-4-amino-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate
其它别名4-N-Desacetyl-5-N-Acetyl Oseltamivir; (3R,4R,5S)-5-(Acetylamino)-4-Amino-3-(1-Ethylpropoxy)-1-Cyclohexene-1-Carboxylic Acid Ethyl Ester; Oseltamivir Ep Impurity G; (3R,4R,5S)-Ethyl 5-Acetamido-4-Amino-3-(Pentan-3-Yloxy)Cyclohex-1-Enecarboxylate; Oseltamivir Phosphate Impurity G (Ep); Oseltamivir Ep Impurity G (Hcl Salt); Oseltamivir Impurity 7(Oseltamivir Ep Impurity G); Oseltamivir Phosphate Ep Impurity G
CAS编号956267-10-0
EINECS号:881-380-2
FDA UNII编号:300BX85SHX
分子式:C16H28N2O4分子量:312.41
产品CID: 2009640
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: SEYYJZMDDOOQNB-RRFJBIMHSA-N
InChI=1S/C16H28N2O4/c1-5-12(6-2)22-14-9-11(16(20)21-7-3)8-13(15(14)17)18-10(4)19/h9,12-15H,5-8,17H2,1-4H3,(H,18,19)/t13-,14+,15+/m0/s1
计算化学: 氢键受体数5.0氢键供体数2.0可旋转键数8.0

物理性质

熔点160-161 °C
沸点473.3±45.0 °C(预测)
密度1.08±0.1 g/cm3(预测)
pKa:14.87±0.70(预测)
PSA:90.65
LogP:2.3766
溶解性Chloroform (Slightly), Ethanol (Slightly), Methanol (Slightly)
外观形态白色至浅米色固体
储存条件冰箱
产品应用该化合物用作分析测试的药品管制呈文.

MSDS等安全信息

GHS象形图
GHS符号GHS07;
注释: Exclamation mark
危险类别急性毒性类别4(吸入)
急性毒性类别4(经皮)
急性毒性类别4(经口)
皮肤腐蚀/刺激类别2
严重眼刺激类别2
警示词Warning(警告)
危险描述H332 |吸入有害.
H312 |皮肤接触有害.
H302 |吞咽有害.
H315 |造成皮肤刺激.
H319 |造成严重眼刺激.

欧盟法规

C&L通报

上下游产品

奥司他韦 Oseltamivir 196618-13-0
(1R,5R,6R)-5-(1-乙丙基)-7-氮杂双环[4.1.0]庚-3-烯-3-羧酸乙酯 Ethyl-(1R,5R,6R)-5-(Pentan-3-Yloxy)-7-Azabicyclo[4.1.0]Hept-3-Ene-3-Carboxylate 204255-02-7
N-脱乙酰基5-叠氮基奥塞米韦 Ethyl (3R,4R,5S)-4-Amino-5-Azido-3-(Pentan-3-Yloxy)Cyclohex-1-Ene-1-Carboxylate 204255-04-9
Ethyl (3R,4R,5S)-5-Azido-4-[(Tert-Butoxycarbonyl)Amino]-3-(1-Ethylpropoxy)Cyclohex-1-Ene-1-Carboxylate 1163128-59-3
Ethyl-(3R,4S,5R)-5-Azido-4-Hydroxy-3-(Pentan-3-Yloxy)Cyclohex-1-Ene-1-Carboxylate 204254-98-8

合成工艺路线路线简述

2254819-34-4 = 956267-10-0
反应条件:1.1 Reagents: Dimethylbarbituric Acid Catalysts: Triphenylphosphine,Palladium Diacetate Solvents: Ethanol; 3 H,35 °C1.2 Reagents: Sodium Carbonate Solvents: Water; Ph 8
标题:Method For Preparing Oseltamivir And Its Isomer
参考文献:World Intellectual Property Organization]

2294915-25-4 = 956267-10-0
反应条件:1.1 Reagents: Trifluoroacetic Acid Solvents: Dichloromethane; 0 - 5 °C; 16 H,25 - 30 °C; 30 °C -> 0 °C1.2 Reagents: Sodium Bicarbonate Solvents: Water; Basified
标题:Synthesis And Characterization Of Potential Pharmacopeial Impurities Of Oseltamivir: An Antiviral Drug
作者:Ponduri,Rajasekhar; Kumar,Pramod; Vadali,Lakshmana Rao; Aelugu,Komaraiah; Matcha,Kishore
参考文献:Asian Journal Of Chemistry 日期:2018 卷标:30(9) 页码:2003-2007]

= 956267-10-0 [标题:Reaction Conditions
标题:Preparation Method Of Acetamido Cyclohexenoate
参考文献:China]

= 956267-10-0 [标题:Reaction Conditions
标题:The First Synthesis Of [11C]Oseltamivir: A Tool For Elucidating The Relationship Between Tamiflu And Its Adverse Effects On The Central Nervous System
作者:Arai,Takuya; Konno,Fujiko; Ogawa,Masanao; Zhang,Ming-Rong; Suzuki,Kazutoshi
参考文献:Journal Of Labelled Compounds And Radiopharmaceuticals 日期:2009 卷标:52(9) 页码:350-354

📜Ethyl (3R,4R,5S)-5-Azido-4-[(Tert-Butoxycarbonyl)Amino]-3-(1-Ethylpropoxy)Cyclohex-1-Ene-1-Carboxylate置于potassium Carbonate,三苯基膦,三氟乙酸体系中,用四氢呋喃,二氯甲烷作为反应溶剂,化学反应 36.0H,反应生成 4-N-脱乙酰基-5-N-乙酰基奥塞米韦
参考文献:奥司他韦的潜在药典杂质的合成和表征:一种抗病毒药物
标题:奥司他韦的潜在药典杂质的合成和表征:一种抗病毒药物
摘要:禽流感在有翼动物中的传播增加了人类完全感染的机会.直到现在,通过个人到个人的传播只是不时地与密切的人类接触保持一致[1].目前,对抗流感的药物包括两类药物:M2 蛋白抑制剂(金刚烷胺和金刚乙胺)和神经氨酸酶抑制剂(奥司他韦和扎那米韦)[2-4].作为一类,神经氨酸酶抑制剂可成功对抗所有神经氨酸酶亚型,因此也可成功对抗所有流感病毒株.这是瘟疫和大流行准备的关键点,并且比 M2 蛋白抑制剂具有必要的有利地位,M2 蛋白抑制剂仅能成功对抗敏感的 A2 流感病毒株.在每一种抗病毒药物中,奥司他韦是治疗禽流感 (H5N1) 感染患者的处方抗病毒药物,并在高危人群中进行化学预防 [5].为了保护人们免受大流行性人类流感或 H5N1 禽流感的侵袭,建议全世界每个国家都应制造和储存磷酸奥司他韦(达菲,图 1)[6,7].由于对这种药物的持续需求,近年来,许多研究人员报告了许多用于制备磷酸奥司他韦的合成序列
DOI:10.14233/ajchem.2018.21376