CAS: 943515-58-0; Ethyl (3Ar,7R,7As)-2,2-Diethyl-7-Hydroxy-3A,6,7,7A-Tetrahydrobenzo[d][1,3]Dioxole-5-Carboxylate
该化合物是一种化学修正的硅酸衍生物,旨在增强合成应用的稳定性和反应性;二乙基甲基乙基和乙酯的功能性组群提高了有机溶剂的溶性,便利其在复杂的有机合成中使用,特别是在制药中间体中;该化合物保留核心的硅酸框架,使其对研究生物合成途径或作为药用化学的前体具有价值;其受保护的氢氧基组群减少了不想要的副反应,确保多步反应更具选择性;结构改变还有助于改善储存寿命,而不是未经修改的硅酸衍生物.
- 英文名称Ethyl (3Ar,7R,7As)-2,2-Diethyl-7-Hydroxy-3A,6,7,7A-Tetrahydrobenzo[d][1,3]Dioxole-5-Carboxylate
- 中文名称3,4-O-(二乙基甲基亚基)莽草酸乙酯
- IUPAC名称ethyl (3aR,7R,7aS)-2,2-diethyl-7-hydroxy-3a,6,7,7a-tetrahydrobenzo[d][1,3]dioxole-5-carboxylate
- 其它别名(3Ar,7R,7As)-Ethyl 2,2-Diethyl-7-Hydroxy-3A,6,7,7A-Tetrahydrobenzo[d][1,3]Dioxole-5-Carboxylate; Oseltamivir Impurity 87; 1,3-Benzodioxole-5-Carboxylic Acid, 2,2-Diethyl-3A,6,7,7A-Tetrahydro-7-Hydroxy-, Ethyl Ester, (3Ar,7R,7As)-; Oseltamivir Impurity 35/ethyl (3Ar,7R,7As)-2,2-Diethyl-7-Hydroxy-3A,6,7,7A-Tetrahydrobenzo[d][1,3]Dioxole-5-Carboxylate; Oseltamivir Impurity 57 (Oseltamivir Impurity）; Ethyl (3Ar,7R,7As)-2,2-Diethyl-7-Hydroxy-3A,6,7,7A-Tetrahydrobenzo[d][1,3]Dioxole-5-Carboxylate; 3,4-O-(Diethylmethylidene) Shikimic Acid Ethyl Ester
- CAS编号943515-58-0
- FDA UNII编号:VRK68QU8Q2
- 分子式:C14H22O5分子量:270.33
- 产品CID: 1993690
- 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
MSDS等安全信息
上下游产品
(3R,4S,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid ethyl ester 3,3-diethoxypentane methyl 2,3-O-isopentylidene-β-D-ribofuranose methyl 5-deoxy-5-iodo-2,3-O-isopentylidene-β-D-ribofuranose ethyl (3aR,7R,7aR)-2,2-dimethyl-7-methanesulfonyloxy-3a,6,7,7a-tetrahydrobenzo[1,3]dioxole-5-carboxylate oseltamivir oseltamivir phosphate ethyl (3R,4R,5R)-3-(1-ethyl-propoxy)-4-hydroxy-5-methanesulfonyloxycyclohex-1-ene-1-carboxylate合成工艺路线路线简述
- 96-22-0 + 101769-63-5 = 943515-58-0
反应条件:1.1 Reagents: Triethyl Orthoformate Catalysts: Benzenesulfonic Acid Solvents: Ethanol; > 3 H,Rt1.2 2 H,Rt
标题:Epoxide Intermediate In The Tamiflu Synthesis
参考文献:World Intellectual Property Organization]
= 943515-58-0
反应条件:1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethanol; 5 D,Rt1.2 Reagents: Sodium Hydride Solvents: Tetrahydrofuran; 0 °C -> Rt; 45 Min,Rt
标题:A Concise And Practical Synthesis Of Oseltamivir Phosphate(Tamiflu) From D-Mannose
作者:Chuanopparat,Nutthawat; Kongkathip,Ngampong; Kongkathip,Boonsong
参考文献:Tetrahedron 日期:2012 卷标:68(34) 页码:6803-6809]
96-22-0 + 138-59-0 = 943515-58-0
反应条件:1.1 Catalysts: Benzenesulfonic Acid Solvents: Ethanol; 15 Min,Rt; 6 - 8 H,Rt -> Reflux; Reflux -> 35 °C1.2 35 °C -> 80 °C; 7 H,78 - 80 °C; 80 °C -> Rt1.3 3 H,25 - 35 °C1.4 Reagents: Triethylamine; Ph 7.5 - 8.5,25 - 35 °C
标题:One Pot Process For The Preparation Of Oseltamivir Phosphate
参考文献:India]
96-22-0 + 101769-63-5 = 943515-58-0 [标题:Reaction Conditions
标题:Shikimic Acid Sulfonates And Preparation Method Thereof
参考文献:China]
96-22-0 + 101769-63-5 = 943515-58-0
反应条件:1.1 3 H,40 - 70 °C
标题:Shikimate Compounds,Shikimic Acid Compounds And Preparation Method Thereof
参考文献:China]
96-22-0 + 138-59-0 = 943515-58-0
反应条件:1.1 Reagents: Phosphorus Trichloride Solvents: 1,2-Dichloroethane; 2 H,25 °C; 4 H,45 °C1.2 Catalysts: Methanesulfonic Acid; 8 H,Reflux1.3 Catalysts: Hydroxyethylenediphosphonic Acid; 1 H,85 °C
标题:New Routes For The Synthesis Of Antiviral Agent Oseltamivir And Its Salts
参考文献:Brazil]
= 943515-58-0 [标题:Reaction Conditions
标题:Method For Preparation Of Shikimate Ether Compounds
参考文献:China]
96-22-0 + 101769-63-5 = 943515-58-0
反应条件:1.1 Catalysts: Trifluoromethanesulfonic Acid Solvents: Ethyl Ketone
标题:Industrial Synthesis Of The Key Precursor In The Synthesis Of The Anti-Influenza Drug Oseltamivir Phosphate (Ro 64-0796/002,Gs-4104-02): Ethyl (3R,4S,5S)-4,5-Epoxy-3-(1-Ethyl-Propoxy)-1-Cyclohexene-1-Carboxylate
作者:Federspiel,Muriel; Fischer,Rolf; Hennig,Michael; Mair,Hans-Juergen; Oberhauser,Thomas; Et Al
参考文献:Organic Process Research & Development 日期:1999 卷标:3(4) 页码:266-274]
96-22-0 + 138-59-0 = 943515-58-0
反应条件:1.1 Catalysts: Benzenesulfonic Acid Solvents: Ethanol; 5 H,Reflux; Cooled1.2 Reagents: Triethyl Orthoformate; 5 H,Reflux; Reflux -> 25 °C1.3 Reagents: Triethyl Orthoformate; 30 Min1.4 Reagents: Triethylamine; Ph 8
标题:Streamlined Process For The Esterification And Ketalization Of Shikimic Acid En Route To The Key Precursor For Oseltamivir Phosphate (Tamiflu)
作者:Carr,Robert; Ciccone,Frank; Gabel,Richard; Guinn,Martin; Johnston,David; Et Al
参考文献:Green Chemistry 日期:2008 卷标:10(7) 页码:743-745]
96-22-0 + 138-59-0 = 943515-58-0
反应条件:1.1 Reagents: Benzenesulfonic Acid,Triethyl Orthoformate Solvents: Ethanol1.2 Reagents: Triethyl Orthoformate
标题:A New Efficient Synthesis Of Oseltamivir Phosphate (Tamiflu) From (-)-Shikimic Acid
作者:Kim,Hee-Kwon; Park,Kyoung-Joo Jenny
参考文献:Tetrahedron Letters 日期:2012 卷标:53(13) 页码:1561-1563]
1884425-64-2 = 943515-58-0
反应条件:1.1 Catalysts: (Sp-5-41)-[1,3-Bis(2,4,6-Trimethylphenyl)-2-Imidazolidinylidene]Dichloro[[2-(1-M... Solvents: 1,2-Dichloroethane; 2 H,Reflux
标题:Synthesis Of Some Carbahexopyranoses Using Mn/crcl3 Mediated Domino Reactions And Ring Closing Metathesis
作者:Kumar,Bejugam Santhosh; Mishra,Girija Prasad; Rao,Batchu Venkateswara
参考文献:Tetrahedron 日期:2016 卷标:72(15) 页码:1838-1849]
= 943515-58-0
反应条件:1.1 Reagents: Sodium Nitrite Solvents: Dimethylformamide; 0 °C; 30 Min,0 °C; 0 °C -> Rt; 3 H,Rt
标题:Expeditious Access To (-)-Shikimic Acid Derivatives For Tamiflu Synthesis
作者:Osato,Hiroshi; Jones,Ian L.; Goh,Huini; Chai,Christina L. L.; Chen,Anqi
参考文献:Tetrahedron Letters 日期:2011 卷标:52(48) 页码:6352-6354]
101769-63-5 + 27154-67-2 = 943515-58-0
反应条件:1.1 Catalysts: P-Toluenesulfonic Acid Solvents: Toluene; 15 Min,100 °C1.2 Reagents: Sodium Bicarbonate Solvents: Water; Rt
标题:Synthesis And In Vitro Study Of Novel Neuraminidase Inhibitors Against Avian Influenza Virus
作者:Kongkamnerd,Jarinrat; Cappelletti,Luca; Prandi,Adolfo; Seneci,Pierfausto; Rungrotmongkol,Thanyada; Et Al
参考文献:Bioorganic & Medicinal Chemistry 日期:2012 卷标:20(6) 页码:2152-2157]
96-22-0 + 101769-63-5 = 943515-58-0 [标题:Reaction Conditions
标题:Method For Crystallizing Intermediate 5 Of Oseltamivir Phosphate With High Purity
参考文献:China]
96-22-0 + 138-59-0 = 943515-58-0
反应条件:1.1 Reagents: Thionyl Chloride Solvents: Ethanol; 1.5 H,Reflux; Cooled1.2 Catalysts: Amberlyst 15 Solvents: Ethyl Ketone; 2.5 H,Rt
标题:New Method For The Rapid Extraction Of Natural Products: Efficient Isolation Of Shikimic Acid From Star Anise
作者:Just,Jeremy; Deans,Bianca J.; Olivier,Wesley J.; Paull,Brett; Bissember,Alex C.; Et Al
参考文献:Organic Letters 日期:2015 卷标:17(10) 页码:2428-2430
📜莽草酸置于氯化亚砜,对甲苯磺酸体系中,用 水,甲苯 作为反应溶剂,化学反应 3.25H,反应生成 3,4-O-(二乙基甲基亚基)莽草酸乙酯
参考文献:新型抗禽流感病毒神经氨酸酶抑制剂的合成及体外研究
标题:新型抗禽流感病毒神经氨酸酶抑制剂的合成及体外研究
摘要:耐奥司他韦的流感患者的证据提出了对新型神经氨酸酶抑制剂的需求.在这项研究中,根据合理设计分析的结果合成了5种奥司他韦类似物pmc-31-Pmc-36,旨在研究奥司他韦的5-氨基和4-酰胺基取代基对其抗病毒活性的影响.筛选其对神经氨酸酶n1和n3的抑制作用.用作模型的酶来自禽流感a H7N1和h7N3病毒.通过使用从杆状病毒表达系统和荧光底物munana获得的重组物种进行神经氨酸酶抑制试验.通过使用奥司他韦羧酸盐作为参考抑制剂来验证该测定.在测试的化合物中,Pmc-36对n1的抑制作用最高,Ic 50为14.6+/-3.0 Nm(奥司他韦25+/-4 Nm),而pmc-35对n3的抑制作用则为ic 500.1+/-0.03 Nm(奥司他韦0.2+/-0.02 Nm).通过对这组化合物的抑制特性进行分析,可以初步评估奥司他韦羧酸酯的4-酰胺基和5-氨基的结构-活性关系.用2-丁烯酰胺基部分取代奥司他韦结构
DOI:10.1016/j.Bmc.2012.01.026
海关参考信息
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专利信息
专利号:US-9150498-B2
优先权日:2011-10-25
标题:Process for the preparation of oseltamivir and methyl 3-epi-shikimate
发明人：RAWAT VARUN; DEY SOUMEN; ARUMUGAM SUDALAI
权利人:COUNCIL SCIENT IND RES
摘要:The present invention discloses high yielding enantioselective process for synthesis of Oseltamivir from readily available starting material, cis-1,4-butene diol. The process features incorporation of chirality using sharpless asymmetric epoxidation (AE) and diastereoselective Barbier allylation and construction of cyclohexene carboxylic acid ester core through a ring closing metathesis (RCM) reaction. Further also disclosed herein is synthesis of (−)-methyl 3-epi-shikimate.
专利号:US-7473798-B2
优先权日:2005-12-28
标题:Derivatives of unsaturated, cyclic organic acids
发明人：GABEL RICHARD A; GROANING MICHAEL D; JOHNSTON DAVID A
权利人:ROCHE PALO ALTO LLC
摘要:The present invention relates to technology for preparing derivatives of unsaturated, cyclic, organic acids and salts, thereof. Shikimic acid is an example of such an acid. More particularly, the present invention relates to preparing derivatives of these acids or salts thereof that are esterified, ketalized, functionalized with a leaving group, and/or provided with epoxide functionality. Preferred aspects may be used in the synthesis of Oseltamivir Phosphate starting from shikimic acid.
