12 results about "Chiral auxiliary" patented technology

The present disclosure, among other things, provides technologies for synthesis, including reagents and methods for stereoselective synthesis. In some embodiments, the present disclosure provides compounds useful as chiral auxiliaries. In some embodiments, the present disclosure provides reagents and methods for oligonucleotide synthesis. In some embodiments, the present disclosure provides reagents and methods for chirally controlled preparation of oligonucleotides. In some embodiments, technologies of the present disclosure are particularly useful for constructing challenging internucleotidic linkages, providing high yields and stereoselectivity.

The invention discloses a chiral phenol calix [4] aryl porous organic molecular cage material as well as a preparation method and application thereof. A chiral calix [4] arene raceme and an acyl chloride chiral auxiliary agent are used as initial raw materials to react to prepare a pair of diastereoisomers, gram-grade separation is achieved through silica gel column chromatography, then the chiral auxiliary agent is removed respectively, and the single enantiomer chiral phenol calix [4] arene compound with the ee value being 99.9% or above can be obtained. The preparation method comprises the following steps of: synthesizing tetraaldehyde chiral phenol calix [4] arene by introducing an aldehyde group unit on the tetraaldehyde chiral phenol calix [4] arene through Duff reaction, and assembling the tetraaldehyde chiral phenol calix [4] arene serving as a construction element with a polyamino organic synthesizer to prepare the chiral phenol calix [4] arene porous organic cage with a larger cavity. The preparation method of the chiral porous organic cage does not need a catalyst, the preparation process is simple, operation is easy and convenient, expansibility is good, the yield is high, and the prepared chiral molecular cage is large in cavity, large in specific surface area and good in repeatability and can be used for chiral recognition and gas adsorption.

The invention provides a method for constructing a chiral axis-containing planar chiral cyclophane compound by activating intramolecular asymmetric carbon-hydrogen bonds under the catalysis of cobalt, which comprises the following steps of: under the action of a cobalt catalyst, a chiral auxiliary agent and an additive, carrying out intramolecular asymmetric C-H activation reaction on alkynyl benzamide, and after the reaction is finished, separating the chiral axis-containing planar chiral cyclophane compound from the alkynyl benzamide to obtain the chiral axis-containing planar chiral cyclophane compound. Separating to obtain a planar chiral cyclophane compound containing a chiral axis; the synthesis of the planar chiral cyclophane compound containing the chiral axis is realized by a transition metal catalyzed asymmetric C-H activation method, the research technology of cheap transition metal catalyzed C-H activation is further developed, and meanwhile, the synthesis strategy of the planar chiral cyclophane compound containing the chiral axis is expanded; according to the present invention, the reaction substrate has characteristics of wide adaptability and strong product stereoselectivity, and the chiral control is achieved through the salicyl oxazoline so as to provide the high enantioselectivity and the high diastereoselectivity of the product; various planar chiral cyclophane compounds containing chiral axes are synthesized, the synthesis method is simple and convenient, the atom economy is good, and the synthesis efficiency is high.

The invention provides a synthesis method of a chiral-axis-containing central chiral aza-seven-membered bridged biaryl compound, which comprises the following steps: under the action of a palladium catalyst, a chiral assistant and an additive, firstly carrying out a carbon-hydrogen bond activation reaction on a benzidine compound under the action of the palladium catalyst, and then reacting with 1, 3-dichlorobenzidine to obtain a chiral-axis-containing central chiral aza-seven-membered bridged biaryl compound. The method comprises the following steps: carrying out asymmetric [5 + 2] cyclization reaction on 1, 3-conjugated diene to obtain a central chiral bridged biaryl compound containing a chiral axis; according to the invention, a palladium-catalyzed asymmetric carbon-hydrogen bond activation / [5 + 2] cyclization method is adopted, so that a new way is provided for synthesizing a chiral seven-membered bridged biaryl structure with fewer reports; sulfoxide oxazoline containing a double chiral source is used as a chiral auxiliary agent, and a single axial product with high diastereoselectivity is obtained in a chiral transfer manner through reaction; the substrate applicability is wide, and a series of central chiral seven-membered bridged biaryl compounds containing chiral shafts are synthesized in a high-yield and high-enantioselectivity manner; the synthesis method is efficient and high in atom economy.

This invention discloses a method for rapid separation and detection of berberine and epiberberine based on ion mobility mass spectrometry. The specific steps are as follows: berberine and epiberberine in the sample to be tested are mixed with cucurbituril [8] and magnesium ions to form a ternary complex; the obtained ternary complex is ionized using an electrospray ionization source; different complex ions are separated using nitrogen as the drift gas in the ion mobility mode; the separated ions are detected by tandem mass spectrometry; qualitative analysis of berberine and epiberberine is achieved based on the triple information of characteristic mass-to-charge ratio, mobility value and collision cross section; and quantitative analysis of berberine and epiberberine is achieved by external standard method or internal standard method. This invention uses cucurbituril [8] as a chiral auxiliary reagent and magnesium ions as a metal complexing agent, and uses ion mobility-mass spectrometry to distinguish berberine isomers, which can rapidly, with high resolution and high accuracy, separate and detect berberine and epiberberine.

The invention provides a method for constructing a planar chiral [2, 2] paracyclophane compound by activating asymmetric carbon-hydrogen bonds under the catalysis of cobalt, which comprises the following steps: under the action of a cobalt catalyst and a chiral assistant, carrying out asymmetric C-H activation reaction on aryl hydrazone and racemic 4-ethynyl-[2, 2] paracyclophane, and carrying out kinetic resolution on the racemic 4-ethynyl-[2, 2] paracyclophane to obtain the planar chiral [2, 2] paracyclophane compound. After the reaction is finished, separation is carried out to obtain planar chiral 4-ethynyl-[2, 2] paracyclophane and a planar chiral 4-isoquinoline-[2, 2] paracyclophane compound; the invention further develops a research technology for catalyzing C-H activation by a cheap transition metal, and expands a synthetic strategy of the planar chiral [2, 2] paracyclophane compound; the reaction substrate is wide in adaptability, and the product is high in stereoselectivity; the multi-planar chiral [2, 2] paracyclophane compound is synthesized, the synthesis method is simple and convenient, the atom economy is good, and the synthesis efficiency is high.

The present application relates to the field of drug synthesis, and more particularly to a preparation method of ezetimibe and intermediates thereof. The synthetic route of the present application utilizes a chiral catalyst 4-pyrrolidinyl pyridine derivative to efficiently construct a beta-lactam parent ring in the molecular structure of ezetimibe, thereby avoiding the use of chiral auxiliary groups in the current process and reducing the cost of the product. The improved route has good process stability, high product total yield and optical purity, and is more suitable for industrial production.

This invention relates to the field of chemical intermediates technology, specifically disclosing a chiral prostaglandin intermediate and its synthesis process. This invention provides a novel synthesis method for chiral prostaglandin intermediates, for example (…). R , E )-3-((tert-butyldiphenylsilyl)oxy)- N -Methoxy- N 4-Methylhexyl-enamide: This process is simple to operate, uses inexpensive raw materials, and has mild reaction conditions, making it suitable for industrial production. The addition of an ethylthio group side arm as a chiral auxiliary improves the chiral control and selectivity of the aldol condensation reaction. It also utilizes inexpensive and readily available ( ) R The formation of chirality is induced by the Evans chiral cofactor of 4-benzyl-2-oxazolidinone. In the Zhang enyne ring isomerization reaction, the catalyst prepared by (Sc,Rp)-Duanphos has high activity and reduces the amount of Rh metal, making the process cost-effective.

The application relates to a method for synthesizing non-azatin and intermediates thereof by using a chiral auxiliary base, and belongs to the technical fields of medicines and chemistry. The application provides a method for synthesizing non-azatin by using a chiral auxiliary base, and the reaction is as follows: wherein R1 is selected from one of the following; X is selected from Cl and Br; the method comprises the following steps: step 3: compound 7 is reacted with compound 8 in the presence of an organic solvent, and an optional dehydrating agent is added to obtain compound 9; step 4: compound 9 is reacted in the presence of a methyl Grignard reagent and an organic solvent to obtain compound 10; step 5: compound 10 is removed from the chiral auxiliary base to obtain compound 11; and step 6: compound 11 is reacted with compound 12 in the presence of a base and an organic solvent to obtain compound 13. The application provides a preparation method for preparing non-azatin and intermediates thereof by using a chiral auxiliary base, and the method has the advantages of high chiral purity, high yield, high purity and good reproducibility.

The invention belongs to the field of medicine synthesis, and provides a method for preparing chiral bicyclol. The method comprises the following steps: (1) carrying out one-step hydrolysis on bifendate in a mixed system of an alkaline buffer solution and an organic solvent to obtain biphenyl ester acid; (2) carrying out amidation on biphenyl ester acid and an Evans chiral prothetic group to obtain a corresponding amide intermediate; and (3) reacting the amide intermediate with a reducing agent to obtain the chiral bicyclol.

The application relates to the technical field of chemical intermediates, and particularly discloses a prostaglandin chiral intermediate and a synthesis process thereof. The application provides a new synthesis process of a prostaglandin chiral intermediate, such as (R, E)-3-((tert-butyldiphenylsilyl)oxy)-N-methoxy-N-methylhex-4-enamide. The process is simple in operation, low in raw material cost and mild in reaction condition, is suitable for industrial production, and has the advantages of better chiral control selectivity of the aldol condensation reaction due to the increase of the ethyl sulfide side arm, the use of cheap and easily available (R)-4-benzyl-2-oxazolidinone Evans chiral auxiliary to induce the formation of chirality, high activity of a catalyst prepared from (Sc, Rp)-Duanphos in the Zhang enyne ring isomerization reaction, and reduction of the Rh metal dosage, so that the process cost has a cost advantage.

The invention discloses a method for preparing carbon isotope labeled levodopa through asymmetric synthesis. The method comprises the following steps: carrying out nucleophilic addition reaction on carbon isotope labeled CO2 and an aryl nucleophilic reagent to obtain carbon isotope labeled pepper acid; carrying out reduction and bromination reaction on piperic acid to synthesize a carbon isotope labeled aryl bromide fragment; the aryl bromide fragment and a chiral auxiliary Schiff base fragment are connected through an asymmetric alkylation reaction, and the carbon isotope labeled levodopa is obtained by removing an auxiliary and a protecting group from a connection product. According to the method, cheap and easily available raw materials are adopted, the cost is low, the yield is high, and the chiral center stereo enantioselectivity is high; according to the method, the L-DOPA can be accurately and stably labeled at the levodopa 3 site at a fixed point, the metabolic stability of the carbon isotope labeled L-DOPA is improved, the asymmetric synthesis of the carbon isotope labeled L-DOPA at the levodopa 3 site is completed for the first time, and a material support is provided for metabolism research related to the levodopa.