126643-10-5

Upstream product

• 93913-62-3 3(R)-methyl-6(S)-<1(R)-methyl-2-(phenylmethoxy)ethyl>-2(S)-(3-oxobutyl)cyclohexanone 
• 93913-63-4 1α-Δ⁵-10α-methyl-7β-<2'β-(1'-benzyloxy)-propyl>-decalone-4 
• 80286-58-4 artemisinic acid 
• 855425-51-3 dihydroartemisinic aldehyde 
• 92692-39-2 (1R,4R,4aS,8aR)-4,7-dimethyl-1-(prop-1-en-2-yl)-1,2,3,4,4a,5,6,8a-octahydronaphthalene 
• 125184-93-2 (R)-2-[(1R,4R,4aS,8aS)-4,7-Dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl]propanal 
• 160454-01-3 <4a(S),8a(S)>-octahydro-5(R)-methyl-8(R)-<1(R)-methyl-2-hydroxyethyl>-2(1H)-naphthalenone 
• 84051-31-0 <1R>-5(R)-methyl-2(S)-<1(R)-methyl-2-(phenylmethoxy)ethyl>cyclohexanol 
• 84051-32-1 (2S,5R)-2-((R)-1-(benzyloxy)propan-2-yl)-5-methylcyclohexanone 
• 7786-67-6 isopulegol 
• 13834-07-6 (1R,3R,4S,8R)-9-hydroxy-p-menthol 
• 917-54-4 methyllithium 
• 103740-02-9 2-(4-methyl-7-oxo-(1α-H),2,3,(4β-H),(4aα-H),5,6,7,8,(8aα-H)-decahydronaphthalen-1-yl)propionic acid 
• 63968-64-9 C₁₂H₁₃O₂(CH₃)3(O)(OO) 

Downstream Products

• 63968-64-9 qinghaosu 
• 105250-95-1 (R)-2-[(1R,2S,3S,4R)-2-Formyl-4-methyl-3-(3-oxo-butyl)-cyclohexyl]-propionic acid 
• 256648-00-7 Toluene-4-sulfonic acid (R)-2-((1R,4R,4aS,8aS)-4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydro-naphthalen-1-yl)-propyl ester 
• 422565-48-8 (R)-2-[(1S,3S,4R)-2-Formyl-2-[(2R,4aS,5R,8S)-8-((R)-1-methoxycarbonyl-ethyl)-2,5-dimethyl-2,3,4,4a,5,6,7,8-octahydro-naphthalen-2-ylperoxy]-4-methyl-3-(3-oxo-butyl)-cyclohexyl]-propionic acid methyl ester 
• 256643-66-0 (1R,2S,3R,6S)-6-Isopropyl-3-methyl-2-(3-oxo-butyl)-cyclohexanecarbaldehyde 
• 103775-34-4 (R)-2-[(1R,2S,3S,4R)-2-Formyl-4-methyl-3-(3-oxo-butyl)-cyclohexyl]-propionic acid methyl ester 
• 63968-64-9 C₁₂H₁₃O₂(CH₃)3(O)(OO) 
• 104196-16-9 (3R,3a,6R,6aS,10aS)-3a,4,5,6,6a,7,8,8a-octahydro-3,6,9-trimethylnaphtho[8a,1-b]furan-2(3H)-one 
• 207446-83-1 arteanniun H 
• 85031-60-3 4α-hydroperoxy-amorph-5-en-12-oic acid 

Relevant academic research and scientific papers

Concise synthesis of artemisinin from a farnesyl diphosphate analogue

Artemisinin is one of the most potent anti-malaria drugs and many often-lengthy routes have been developed for its synthesis. Amorphadiene synthase, a key enzyme in the biosynthetic pathway of artemisinin, is able to convert an oxygenated farnesyl diphosphate analogue directly to dihydroartemisinic aldehyde, which can be converted to artemisinin in only four chemical steps, resulting in an efficient synthetic route to the anti-malaria drug.

Preparation method for key intermediate for synthesis of artemisinin compounds

The invention relates to the technical field of organic chemical engineering, in particular to an asymmetric preparation method for synthesizing an artemisinin compound synthesis key intermediate dihydroartemisinic acid. When the intermediate is applied to synthesis of artemisinin compounds, the operation is simple and convenient, the yield and the product purity are improved, and industrial application is easy.

Online Stereochemical Process Monitoring by Molecular Rotational Resonance Spectroscopy

A molecular rotational resonance (MRR) spectrometer designed to monitor the product composition of an asymmetric continuous flow reaction online is presented. The MRR technique is highly sensitive to small changes in molecular structure and, as such, is capable of rapidly quantifying isomers as well as other impurities in a complex mixture, without chromatographic separation or chemometrics. The spectrometer in this study operates by automatically drawing a portion of the reaction solution into a reservoir, volatizing it by heating, and measuring the highly resolved MRR spectra of each of the components of interest in order to determine their relative quantity in the mixture. The reaction under study was the hydrogenation of artemisinic acid, an intermediate step in the semisynthesis of the antimalarial drug artemisinin. Four analytes were characterized in each measurement: the starting material, the product, a diastereomer of the product, and an overreduction byproduct that was not directly quantifiable by either HPLC or NMR methods. The MRR instrument has a measurement cycle time of approximately 17 min for this analysis and can run for several hours without any user interaction.

Chemical semi-synthesis method of artemisinin

The invention provides a chemical semi-synthesis method of artemisinin represented by a formula (VI) shown in the specification. The chemical semi-synthesis method comprises the following specific steps: (1) reacting dihydroartemisinic acid represented by a formula (I) shown in the specification with oxalyl chloride represented by a formula (II) shown in the specification to generate dihydroartemisinyl chloride represented by a formula (III) shown in the specification; (2) carrying out an acylation reaction on the dihydroartemisinyl chloride represented by the formula (III) and dihydroarteannuic acid represented by a formula (I) shown in the specification to generate dihydroarteannuic anhydride represented by a formula (IV) shown in the specification; and (3) carrying out a photooxidationreaction on the dihydroarteannuic anhydride represented by the formula (IV) by using a micro-channel reactor, and carrying out an oxidation rearrangement reaction to prepare the target product artemisinin represented by the formula (VI). Compared with the prior art, the method provided by the invention has the advantages of a high product yield, good purity of the product, a stable process, mild reaction conditions, easiness in industrial production and the like.

Preparation method of artemisinin

The invention discloses a preparation method of artemisinin, wherein the preparation method comprise the steps: with artemisinic acid as a starting material, obtaining dihydroartemisinic acid under the hydrogen/metal catalyst action, then oxidizing dihydroartemisinic acid into arteannuic acid dihydrogen peroxide by hydrogen peroxide in the presence of sodium molybdate, and finally acting with oxygen under the catalysis of copper trifluoromethanesulfonate, to obtain the target product artemisinin with high yield. Compared with the prior art, the preparation method has the following advantages:the used reagents are cheap and easy to get, the synthetic route is short, the reaction selectivity is high, the preparation process is environmentally friendly, the operation and post-processing aresimple, the total yield is high, and the preparation method is suitable for industrialized production.

An Efficient Chemoenzymatic Synthesis of Dihydroartemisinic Aldehyde

Artemisinin from the plant Artemisia annua is the most potent pharmaceutical for the treatment of malaria. In the plant, the sesquiterpene cyclase amorphadiene synthase, a cytochrome-dependent CYP450, and an aldehyde reductase convert farnesyl diphosphate (FDP) into dihydroartemisinic aldehyde (DHAAl), which is a key intermediate in the biosynthesis of artemisinin and a semisynthetic precursor for its chemical synthesis. Here, we report a chemoenzymatic process that is able to deliver DHAAl using only the sesquiterpene synthase from a carefully designed hydroxylated FDP derivative. This process, which reverses the natural order of cyclization of FDP and oxidation of the sesquiterpene hydrocarbon, provides a significant improvement in the synthesis of DHAAl and demonstrates the potential of substrate engineering in the terpene synthase mediated synthesis of high-value natural products.

Dihydroartemisinic acid synthesis technology

The invention discloses a dihydroartemisinic acid synthesis technology. The technology comprises dissolving dihydroartemisinic acid in an organic solvent, adding hydrazine hydrate and a catalytic amount of a transition metal compound into the solution, adjusting a reaction temperature in a range of 65-100 DEG C, dropwisely adding hydrogen peroxide into the reaction solution so that the arteannuic acid is reduced into dihydroartemisinic acid through diimine produced in situ, and carrying out extraction and drying to obtain dihydroartemisinic acid. The technology has short synthesis reaction time and a high dihydroartemisinic acid yield.

Asymmetric Hydrogenation of α-Substituted Acrylic Acids Catalyzed by a Ruthenocenyl Phosphino-oxazoline-Ruthenium Complex

Asymmetric hydrogenation of various α-substituted acrylic acids was carried out using RuPHOX-Ru as a chiral catalyst under 5 bar H2, affording the corresponding chiral α-substituted propanic acids in up to 99% yield and 99.9% ee. The reaction could be performed on a gram-scale with a relatively low catalyst loading (up to 5000 S/C), and the resulting product (97%, 99.3% ee) can be used as a key intermediate to construct bioactive chiral molecules. The asymmetric protocol was successfully applied to an asymmetric synthesis of dihydroartemisinic acid, a key intermediate required for the industrial synthesis of the antimalarial drug artemisinin.

A method for synthesizing hydrogen southernwood acid

A synthetic method for dihydroartemisinin comprises the following steps: dissolving arteannuic acid in an organic solvent, then adding hydrazine hydrate and a transition metal compound capable of forming a coordination compound with hydrazine hydrate, adjusting the reaction temperature to 25 DEG C-100 DEG C, then introducing oxygen or air into the reaction solution, so as to reduce arteannuic acid to generate dihydroartemisinin by in-situ generated diimine, and performing extraction and drying to obtain dihydroartemisinin. The synthetic method has the characteristics of being less in raw material usage amount, high in yield, short in reaction time and low in energy consumption.

A method for preparing hydrogen southernwood acid

The invention relates to a dihydroarteannuic acid preparation method, which comprises: dissolving arteannuic acid in an organic solvent, adding hydrazine hydrate with any concentration and a catalytic amount of a guanidinium, adjusting the reaction temperature to 25-100 DEG C, adding hydrogen peroxide with any concentration to the reaction solution in a dropwise manner or introducing oxygen to generate diimine in an in situ manner so as to make the arteannuic acid be reduced into the dihydroarteannuic acid by the diimine produced in the in situ manner, extracting and drying to obtain the dihydroarteannuic acid. The preparation method has characteristics of low energy consumption, short reaction time, simple preparation process and high dihydroarteannuic acid yield, and is suitable for large-scale industrial production.