45 results about "Swern oxidation" patented technology

The invention relates to a preparation method of paricalcitol, which is characterized in that after hydroxyl in the vitamin D2 is protected by p-toluenesulfonates, in the presence of alkali, intramolecular cyclization reaction happens in methanol to generate a compound 5; the compound 5 undergoes allylic oxidation and hydroxyl is protected to obtain a key intermediate 7; in the presence of ozone,the side chains and exocyclic terminal double bonds of the key intermediate 7 are cut off to obtain a compound 8; the primary hydroxyl in the compound 8 is selectively protected, a three-membered ring is opened in the presence of acid and then hydroxyl is protected to obtain a key intermediate 11; after the secondary hydroxyl in the key intermediate 11 is protected by sulphonate, a compound 12 isobtained through reduction by LiAlH4; a compound 13 is obtained after the compound 12 is subjected to Swern oxidation and carries out Wittig reaction with the compound 12 to obtain a compound 14; andthe target compound can be obtained by removing the protective group in the compound 14. The reagents used in the method are simple and are convenient to operate, the reactions concerning regioselectivity and stereoselectivity are few, the route is shorter and 12 steps of reactions are carried out.

The invention provides a tulathromycin intermediate, a preparation method of the tulathromycin intermediate, and a preparation method of the tulathromycin. The preparation method of the tulathromycin has the advantages of mild condition, convenience for operation, and low cost. The preparation method of the tulathromycin comprises the following steps of: using azithromycin A as a raw material; protecting 2'-hydroxy and 6'-amino in the azithromycin A through di-tert-butyl dicarbonate so as to obtain double-protective azithromycin A; carrying out Swern oxidation to 4''-hydroxy to the double-protective azithromycin A; salifying along with trifluoroacetic acid; and synchronously removing boc t-butyloxycarbonyl to obtain the azithromycin A bitrifluoroacetic acid salt of 4''-carbonyl; and then reacting with trimethylsulfonium bromide to obtain 4''-epoxy compound; and finally carrying out nucleophilic addition on the 4''-epoxy compound by n-propylamine so as to obtain the phosphate of tulathromycin; and further neutralizing via alkaline to obtain the target compound tulathromycin; and synchronously obtaining the tulathromycin intermediate of azithromycin A bitrifluoroacetic acid salt of 4''-carbonyl.

A sulphonyl tetrazole compound 7 with the following structure, its preparation method and its use for preparing laetispicine. The said sulphonyl tetrazole compound 7, (1-phenyl-5-(3,4-methylenedioxyphenyl ethyl) sulphonyl tetrazole), is obtained from piperonal as raw material and by steps of Darzens condensation, hydrolysis, decarboxylation, reduction, condensation and oxidation. Laetispicine is prepared from the said compound as raw material, by condensation with 9-carbonyl-2E-4E-nonadienoic acid isobutyramide (compound 14), or by reaction with 5-(tetrahydropyran-2-oxo) n-pentanal (compound 10), deprotection, Swern oxidation, Wittig-Horner reaction, hydrolysis and amidation. As shown in H NMR, C NMR, MS and IR, the laetispicine prepared from the above-said compound is consistent with the laetispicine extracted from natural products.

The invention relates to a new synthesis route and method of a bedaquiline racemate, belonging to the technical field of medicine. Its steps include: (1) starting material 3-bromobenzyl-6-bromo-2-methoxyquinoline (II) reacts with metal magnesium in THF to prepare Grignard reagent, and then 1-naphthaldehyde (III ) is added in the prepared Grignard reagent, and the reflux reaction obtains the compound (Ⅳ) "2-(6-bromo-2-methoxyquinoline-3-yl)-1-(naphthalene-1-yl)-2- Phenyl alcohol "; (2) make compound (IV) undergo swern oxidation to obtain carbonyl compound 2-(6-bromo-2-methoxyquinoline-3-yl)-1-(naphthalene-1-yl)-2 ‑Phenyl ethyl ketone (compound V); (3) Compound (V) reacts with Grignard reagent (VI) to obtain bedaquiline racemate (I). The method of the invention has simple and convenient route, mild reaction conditions, low cost and high yield, and is suitable for industrial production and application.

The invention relates to a method for preparing a clausenamide intermediate by a Swern oxidation process and belongs to the field of pharmaceutical chemicals. The method comprises a step of oxidizing N-methyl-N-(2-hydroxy-2-phenyl)ethyl-3-phenylglycidylamide (I) compound under an alkaline condition in a solvent to obtain a N-methyl-N-benzoylmethyl-3-phenylglycidylamide(II) compound.

The invention discloses a 4-(2-(2-(methylsulfoxide)ethyl)-4-nitrophenyl)morpholine represented by formula (I), and discloses its preparation and application. Its preparation method is as follows: 2-(2-chloro-5 nitro)phenethyl alcohol and morpholine as shown in formula (II) are mixed to obtain 2-(2-morpholine-5 as shown in formula (III) -Nitrophenyl) ethanol; Then in (III), add dropwise two (trichloromethyl) carbonates successively, sodium methyl mercaptide aqueous solution, hydrogen peroxide aqueous solution, finally make 4-(2-(2-(form (sulfoxide)ethyl)-4-nitrophenyl)morpholine. Its application is to react the obtained swern reagent with the alcohol compound shown in formula (IV), and prepare the aldehyde or ketone shown in formula (V) through post-treatment. The present invention overcomes the shortcomings of the existing Swern oxidation method, avoids the generation of foul-smelling by-products dimethyl sulfide and toxic carbon monoxide from the source, increases the reaction temperature to -30°C to 0°C, and has no odor The by-product new sulfide can be recovered and reused.

The invention relates to a preparation method of L-lyxose and relates to a five-carbon sugar. The invention provides a preparation method of L-lyxose and the method has cheap and easily available raw materials, fewer reagents and simple process. The technical scheme of the preparation method uses L-arabinose as a raw material; L-arabinose is subjected to hydroxyl protection and is reduced into a sugar alcohol, then the molecular configuration is changed under Swern oxidation condition, and finally the product L-lyxose with mirror symmetry conversion is obtained. The method comprises the following steps: synthesizing 5-O-triphenylmethyl-L-arabinose (2); synthesizing 5-O-triphenylmethyl-L-arabitol (3); synthesizing 5-O-triphenylmethyl-1,2,3,4-tetraacetylarabitol (4); synthesizing L-arabitol-1,2,3,4-tetraacetate (5); synthesizing L-lyxose-2,3,4,5-tetraacetate (6); and synthesizing L-lyxose (7).

The invention relates to a method for asymmetric synthesis of chain nonsaturated ester IeodomycinA and B. The method utilizes geraniol as a raw material and through Swern oxidation, 3-chloroperbenzoic acid epoxidation reaction, Wittig reaction and periodic acid oxidation cutting-off reaction, an intermediate 5 is prepared. Through a two-step reaction with trimethylchlorosilane, methyl acetoacetate as an intermediate 2 is prepared. Silyl enol ether 8 and aldehyde 5 are synthesized into a key intermediate 9 in the presence of a titanium tetraisopropanolate / (S)-BINOL as a catalyst. Through hydroxyl-induced reduction reactions, the end product IeodomycinA and B are synthesized. The method comprises the eight steps, has a simple and reasonable design, utilizes cheap raw materials and has a high product yield. The IeodomycinA and B have high optical purity.

The invention belongs to the field of chemical synthesis. The invention relates to a method of synthesis of 6-deoxy-L-talose,including: 1) performing glucoside protection of 1-positon hydroxyl of L-rhamnose in methanol solution by utilizing cation exchange resin (732H+type) to obtain a compound; 2) performing isopropylidene protection of hydroxyls at 2 and 3 positions of the compound to obtain a compound; 3) oxidizing 4-position hydroxyl of the compound to a ketone carbonyl group by utilizing a Swern oxidation system, so as to obtain a compound; 4) performing stereoselective reduction of 4-position carbonyl of the compound by utilizing sodium borohydride or sodium cyanoborohydride, so as to obtain a precursor compound with an opposite configuration to the raw materials, of 6-deoxy-L-talose; 5) refluxing the compound in sulfuric acid aqueous solution to hydrolyze to obtain 6-deoxy-L-talose. The preparing method using easily-available L-rhamnose having low price as the initial raw material, is a simple method, and is utility and efficient.

The invention discloses a novel compound that is 6,6-dimethyl tetrahydropyran-2-methanol and a preparing method thereof. The method includes preparing benzyloxy ethanol by utilizing a sodium alkoxideprocess; then oxidizing the benzyloxy ethanol into benzyloxy acetaldehyde by utilizing a swern oxidation process; reacting the benzyloxy acetaldehyde and allyltributyltin prepared by utilizing a Grignard reaction to obtain 1-(benzyloxy)-4-penten-2-ol; subjecting the 1-(benzyloxy)-4-penten-2-ol and acetone to cyclization under catalysis of trimethylchlorosilane and potassium iodide to obtain 4-iodo-6,6-dimethyl tetrahydropyran-2-methanol; and subjecting the 4-iodo-6,6-dimethyl tetrahydropyran-2-methanol to hydrogenation to remove iodine to obtain the target product that is the 6,6-dimethyl tetrahydropyran-2-methanol. According to the method, reactions are relatively mild, products can be easily treated and purified, and the method is suitable for batch preparation, and therefore the methodhas important application value.

The invention belongs to the technical field of medicine synthesis, and relates to a preparation method of a novel anticancer medicine lanosterol derivative. In this method, lanosterol is used as the starting material and protected by tert-butyldimethylsilyl (TBS) to generate intermediate LD-a, and intermediate LD-a undergoes Sharpless asymmetric dihydroxylation under the action of osmium tetroxide (OsO4) The reaction generates the diol compound LD-b, and the LD-b compound undergoes Swern oxidation under triethylamine basic conditions to generate the α-hydroxy ketone compound LD-c, and the acylation reaction between LD-c and acetic anhydride gives the intermediate LD ‑d, LD‑b were deprotected by TBS to obtain the intermediate LD‑e, and finally epoxidized to obtain the target lanosterol derivative LD. The reaction conditions of each step of the invention are relatively mild, the synthesis steps are short, the use of highly toxic or expensive reagents is avoided, and the obtained product has high purity, which can be used in industrial production.