CAS: 85031-59-0; (R)-2-((1R,4R,4As,8As)-4,7-Dimethyl-1,2,3,4,4A,5,6,8A-Octahydronaphthalen-1-yl)Propanoic Acid

结构式图片

物理性质

MSDS等安全信息

欧盟法规

C&L通报

上下游产品

Dihydroartemisinic Aldehyde 125184-93-2
Dihydroartemisinic Aldehyde 855425-51-3
青蒿酸 Artemisinic Acid 80286-58-4
2-(4-Methyl-7-Oxo-(1α-H),2,3,(4β-H),(4Aα-H),5,6,7,8,(8Aα-H)-Decahydronaphthalen-1-yl)Propionic Acid 103740-02-9
Amorpha-4,11-Diene 92692-39-2

合成工艺路线路线简述

  • 125184-93-2 = 85031-59-0
    反应条件:1.1 Reagents: Monosodium Phosphate,Sodium Hypochlorite Solvents: Dimethyl Sulfoxide,Water; 4 H,Rt1.2 Reagents: Phosphoric Acid Solvents: Water; Ph 2
    标题:A Novel Semi-Biosynthetic Route For Artemisinin Production Using Engineered Substrate-Promiscuous P450Bm3
    作者:Dietrich,Jeffrey A.; Et Al
    参考文献:Acs Chemical Biology 日期:2009 卷标:4(4) 页码:261-267]

    647032-75-5 = 85031-59-0
    反应条件:1.1 Reagents: Hydrogen Peroxide,Hydrazine Hydrate (1:1) Solvents: Isopropanol,Water; 3.5 H,30 - 32 °C; 6 - 7 H,30 - 32 °C1.2 Reagents: Hydrochloric Acid Solvents: Water; Ph 3,25 - 30 °C2.1 Reagents: Biphenyl,Lithium Solvents: 1,2-Dimethoxyethane; Rt -> 85 °C; 10 H,80 - 85 °C; 85 °C -> 5 °C2.2 Solvents: Water; 1 H,0 - 5 °C; 2 H,20 - 25 °C2.3 Solvents: Toluene; 30 Min,20 - 25 °C2.4 Reagents: Hydrochloric Acid Solvents: Water; Ph 3.5 - 4
    标题:Amalgamation Of Synthetic Biology And Chemistry For High-Throughput Nonconventional Synthesis Of The Antimalarial Drug Artemisinin
    作者:Singh,Dharmendra; Et Al
    参考文献:Organic Process Research & Development 日期:2017 卷标:21(4) 页码:551-558]

    93913-65-6 = 85031-59-0 [标题:Reaction Conditions
    标题:Asymmetric Synthesis Of Dihydroartemisinic Acid Through Intramolecular Stetter Reaction
    作者:Rej,Rohan Kalyan; Et Al
    参考文献:Tetrahedron 日期:2016 卷标:72(32) 页码:4931-4937]

    93913-65-6 = 85031-59-0
    反应条件:1.1 Reagents: Sodium,Ammonia Solvents: Diethyl Ether2.1 Reagents: Chromium Trioxide,Sulfuric Acid Solvents: Acetone,Water
    标题:Total Synthesis Of Arteannuin And Deoxyarteannuin
    作者:Xu,Xingxiang; Et Al
    参考文献:Tetrahedron 日期:1986 卷标:42(3) 页码:819-28]

    125276-60-0 = 85031-59-0 [标题:Reaction Conditions
    标题:Synergistic Effect Of Coronatine And Sorbitol On Artemisinin Production In Cell Suspension Culture Of Artemisia Annua L. Cv. Anamed
    作者:Salehi,Maryam; Et Al
    参考文献:Plant Cell 日期:2019 卷标:137(3) 页码:587-597]

    855425-51-3 = 85031-59-0
    反应条件:1.1 Reagents: Monosodium Phosphate,Sodium Hypochlorite Solvents: Dimethyl Sulfoxide,Water; 2 H,Rt; 2 H,Rt1.2 Reagents: Sodium Bicarbonate Solvents: Water; 15 H,Rt1.3 Reagents: Phosphoric Acid; Ph 2
    标题:Production Of Amorphadiene In Yeast,And Its Conversion To Dihydroartemisinic Acid,Precursor To The Antimalarial Agent Artemisinin
    作者:Westfall,Patrick J.; Et Al
    参考文献:Proceedings Of The National Academy Of Sciences Of The United States Of America 日期:2012 卷标:109(3)]

    855425-51-3 = 85031-59-0 [标题:Reaction Conditions
    标题:Synergistic Effect Of Coronatine And Sorbitol On Artemisinin Production In Cell Suspension Culture Of Artemisia Annua L. Cv. Anamed
    作者:Salehi,Maryam; Et Al
    参考文献:Plant Cell 日期:2019 卷标:137(3) 页码:587-597]

    = 85031-59-0
    反应条件:1.1 Reagents: Biphenyl,Lithium Solvents: 1,2-Dimethoxyethane; Rt -> 85 °C; 10 H,80 - 85 °C; 85 °C -> 5 °C1.2 Solvents: Water; 1 H,0 - 5 °C; 2 H,20 - 25 °C1.3 Solvents: Toluene; 30 Min,20 - 25 °C1.4 Reagents: Hydrochloric Acid Solvents: Water; Ph 3.5 - 4
    标题:Amalgamation Of Synthetic Biology And Chemistry For High-Throughput Nonconventional Synthesis Of The Antimalarial Drug Artemisinin
    作者:Singh,Dharmendra; Et Al
    参考文献:Organic Process Research & Development 日期:2017 卷标:21(4) 页码:551-558]

    106549-22-8 = 85031-59-0
    反应条件:1.1 Reagents: Chromium Trioxide,Sulfuric Acid Solvents: Acetone,Water
    标题:Total Synthesis Of Arteannuin And Deoxyarteannuin
    作者:Xu,Xingxiang; Et Al
    参考文献:Tetrahedron 日期:1986 卷标:42(3) 页码:819-28]

    106549-22-8 = 85031-59-0
    反应条件:1.1 Reagents: Triethylamine,Sulfur Trioxide-Pyridine Solvents: Dimethyl Sulfoxide,Dichloromethane; 20 Min,-10 °C; -10 °C -> Rt; 15 H,Rt2.1 Reagents: Monosodium Phosphate,Sodium Hypochlorite Solvents: Dimethyl Sulfoxide,Water; 4 H,Rt2.2 Reagents: Phosphoric Acid Solvents: Water; Ph 2
    标题:A Novel Semi-Biosynthetic Route For Artemisinin Production Using Engineered Substrate-Promiscuous P450Bm3
    作者:Dietrich,Jeffrey A.; Et Al
    参考文献:Acs Chemical Biology 日期:2009 卷标:4(4) 页码:261-267]

    855425-50-2 = 85031-59-0
    反应条件:1.1 Reagents: Triethylamine,Sulfur Trioxide-Pyridine Complex Solvents: Dimethyl Sulfoxide,Dichloromethane; Rt -> -10 °C; 60 Min,-10 °C; 15 H,Rt2.1 Reagents: Monosodium Phosphate,Sodium Hypochlorite Solvents: Dimethyl Sulfoxide,Water; 2 H,Rt; 2 H,Rt2.2 Reagents: Sodium Bicarbonate Solvents: Water; 15 H,Rt2.3 Reagents: Phosphoric Acid; Ph 2
    标题:Production Of Amorphadiene In Yeast,And Its Conversion To Dihydroartemisinic Acid,Precursor To The Antimalarial Agent Artemisinin
    作者:Westfall,Patrick J.; Et Al
    参考文献:Proceedings Of The National Academy Of Sciences Of The United States Of America 日期:2012 卷标:109(3)]

    125184-95-4 = 85031-59-0 [标题:Reaction Conditions
    标题:Synergistic Effect Of Coronatine And Sorbitol On Artemisinin Production In Cell Suspension Culture Of Artemisia Annua L. Cv. Anamed
    作者:Salehi,Maryam; Et Al
    参考文献:Plant Cell 日期:2019 卷标:137(3) 页码:587-597
📜青蒿素置于双氧水,一水合肼体系中,化学反应生成 二氢青蒿酸
参考文献:二氢青蒿酸合成工艺
标题:二氢青蒿酸合成工艺
摘要:本发明公开了一种二氢青蒿酸合成工艺,步骤如下:将青蒿酸溶于有机溶剂中,然后,加入水合肼和催化量的过渡金属化合物,调节反应温度至65oc~100°C,再向反应液中滴加双氧水,使青蒿酸被原位产生的二亚胺还原为二氢青蒿酸,经萃取,干燥,得到二氢青蒿酸.本发明合成反应时间短,二氢青蒿酸的收率高.

海关参考信息

专利信息


专利号:US-2025214918-A1
优先权日:2022-05-20
标 题:Functionalization of terpenes by selective deprotonation for the synthesis of (+)-artemisinin and related compounds
发明人：FRANTZ DOUG E; BLUMBERG SHAWN; ORTIZ ELIEZER; CLANTON NICHOLAS; WILSON NICK
权利人:UNIV TEXAS
摘要:The present invention provides methods for the preparation of (+)-Artemisinin and intermediates thereof, including via the regioselective deprotonation of amorphadiene (AD). In other aspects, there are provided methods for the functionalization terpenes by selective deprotonation, including the utilization of 4,11-amorphadiene as an industrially viable feedstock for the synthesis of artemisinin. In some embodiments, these methods are broadly applicable to the derivatization of a variety of cyclic and linear terpenes.

专利号:WO-2015030681-A1
优先权日:2013-08-30
标题:In vitro synthetic multi-biocatalytic system for the synthesis of isoprenoids and isoprenoid precursors
发明人：TOO HENG PHON; CHEN XIXIAN; ZOU RUIYANG; ZHANG CONQIANG
权利人:UNIV SINGAPORE
摘要:Disclosed herein are in vitro multi-biocatalytic systems for the synthesis of isoprenoid precursors and isoprenoids, as well as methods of producing isoprenoid precursors or isoprenoids in vitro using the systems disclosed herein.

专利号:US-7541172-B2
优先权日:1998-08-27
标题:Transgenic amorpha-4, 11-diene synthesis
发明人：WALLAART THORVALD EELCO; BOUWMEESTER HENDRIK JAN
权利人:INST ONEWORLD HEALTH
摘要:The present invention relates to an isolated DNA sequence encoding a polypeptide having the biological activity of amorpha-4,11-diene synthase. This DNA sequence can be used for the transformation of bacteria, yeasts and plants for the production of amorpha-4,11-diene, a specific precursor in the synthesis of artemisinin, in the respective organisms. The invention also relates to these organisms.

专利号:US-9802952-B2
优先权日:2013-07-15
标 题:Method and apparatus for the synthesis of dihydroartemisinin and artemisinin derivatives
发明人：KOPETZKI DANIEL; MCQUADE DAVID TYLER; SEEBERGER PETER H; GILMORE KERRY
权利人:MAX-PLANCK-GESELLSCHAFT ZUR FÖRDERUNG DER WSS E V; MAX-PLANK-GESELLSCHAFT ZUR FÖRDERUNG DER WSS E V
摘要:The present invention is directed to a method for continuous production of dihydroartemisinin and also artemisinin derivatives derived from dihydroartemisinin by using artemisinin or dihydroartemisinic acid (DHAA) as starting material as well as to a continuous flow reactor for producing dihydroartemisinin as well as the artemisinin derivatives. It was found that the reduction of artemisinin to dihydroartemisinin in a continuous process requires a special kind of reactor and a special combination of reagents comprising a hydride reducing agent, at least one activator such as an inorganic activator, at least one solid base, at least one aprotic solvent and at least one C 1 -C 5 alcohol.

专利号:WO-2023225681-A9
优先权日:2022-05-20
标题:S hopingfunctionalization of terpenes by selective deprotonation for the synthesis of (+)-artemisinin and related compounds

专利号:EP-3022208-A1
优先权日:2013-07-15
标题 :Method and apparatus for the synthesis of dihydroartemisinin and artemisinin derivatives

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合成参考文献


摘要:Quin, M. B.; Flynn, C. M.; Ellinger, J. J.; Schmidt-Dannert, C., Science of Synthesis: Biocatalysis in Organic Synthesis, (2015) 3, 369.
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