407577-54-2

Usage

Uses

Used in Pharmaceutical Industry:
(4R,6R)-6-HydroxyMethyl-2,2-diMethyl-1,3-dioxane-4-acetic Acid 1,1-DiMethylethyl Ester is used as a synthetic intermediate for the production of Rosuvastatin (R700500) and its derivatives. Rosuvastatin is a widely prescribed medication for the treatment of high cholesterol and related cardiovascular conditions. (4R,6R)-6-HydroxyMethyl-2,2-diMethyl-1,3-dioxane-4-acetic Acid 1,1-DiMethylethyl Ester's role in the synthesis of Rosuvastatin highlights its importance in the development of effective therapies for managing cholesterol levels and reducing the risk of heart disease.

Upstream product

• 1694-31-1 tert-butyl acetoacetate 
• 143827-05-8 (3R,5S)-3,5-Dihydroxy-5-((2S,3S)-3-trimethylsilanyl-oxiranyl)-pentanoic acid tert-butyl ester 
• 1067638-10-1 C₁₈H₃₂O₆ 
• 406680-96-4 tert-butyl (5S)-6-chloro-3,5-dihydroxyhexanoate 
• 521973-99-9 tert-butyl 2-((6S)-6-(chloromethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate 
• 154026-92-3 Tert-butyl (5S)-6-chloro-5-hydroxy-3-oxohexanoate 
• 154026-93-4 1,1-dimethylethyl (3R,5S)-6-chloro-3,5-dihydroxy-4-hexanoate 
• 154026-94-5 (4R-cis)-6-(chloromethyl)-2,2-dimethyl-1,3-dioxane-4-acetic acid,1,1-dimethylethyl ester 
• 623566-51-8 tert-butyl (S)-4-(propylene oxide-2-yl)-3-oxobutanoate 
• 147849-64-7 tert-butyl (S)-6-(benzyloxy)-5-hydroxy-3-oxohexanoate 
• 1044518-94-6 tert-butyl 2-((4S,6R)-6-[(tert-butyl)dimethylsilyloxymethyl]-2,2-dimethyl-1,3-dioxan-4-yl)acetate 
• 521973-99-9 (4R-cis)-6-chloromethyl-2,2-dimethyl-1,3-dioxane-4-acetic acid tert-butyl ester 
• 140235-45-6 2-ethoxycarbonyl-4-tert.-butoxycarbonylmethyl-6,6-dimethyl-1,5-dioxane 
• 140235-31-0 2-methoxycarbonyl-4-tert.-butoxycarbonylmethyl-6,6-dimethyl-1,5-dioxane 

Downstream Products

• 147489-06-3 (4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester 
• 132895-31-9 (4R,6S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-4-hydroxy-tetrahydro-pyran-2-one 
• 132895-33-1 (4S,6S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-4-hydroxy-tetrahydro-pyran-2-one 
• 1044518-75-3 (4R-cis)-6-formyl-2,2-dimethyl-1,3-dioxane-4-acetic acid tert-butyl ester 
• 131666-49-4 (2S,4R)-6-tert-butoxy-2,4-dihydroxy-6-oxohexyl benzoate 
• 1007871-85-3 tert-butyl-6-[(1E)-2-[4-(4-fluorophenyl)-6-(1-methylethyl)-2-[methyl(methylsulfonyl)amino]-5-pyrimidinyl]ethenyl]-2,2-dimethyl-1,3-dioxane-4-acetate 

Relevant academic research and scientific papers

Preparation method of rosuvastatin calcium intermediate

The invention belongs to the technical field of medicinal chemistry and relates to the technical field of drug synthesis, particularly to a preparation method of a high-purity rosuvastatin calcium intermediate. The preparation method of the high-purity rosuvastatin calcium intermediate comprises controlling reaction PH and temperature and applied amount of sodium hypochlorite to control the content of impurities in the high-purity rosuvastatin calcium intermediate shown as the formula I', thereby improving the yield and purity of finished products. The content of impurity compound I' in the high-purity rosuvastatin calcium intermediate prepared through the method is lower than 0.05%. The preparation method of the high-purity rosuvastatin calcium intermediate is highly significant to quality improvement of industrialized production products of the high-purity rosuvastatin calcium intermediate, and further achieves certain assisting and supporting effects on quality improvement as well as registration and declaration of rosuvastatin calcium drugs.

Preparation method of rosuvastatin calcium intermediate

Preparation method of rosuvastatin calcium intermediateTo the preparation method of the compound CL - 9, the compound CL - 8 is subjected to organic alkali treatment to obtain the compound CL - 9. The compound CL - 9 prepared through the route has the advantages of high yield, high purity, controllable impurities, suitability for industrial production and the like.

Chemical synthesis method of rosuvastatin intermediate

The invention belongs to the technical field of pharmaceutical chemicals, and particularly relates to a chemical synthesis method of a rosuvastatin intermediate. The method comprises the steps: takinga compound (4R-cis)-6-chloromethyl-2,2-dimethyl-1,3-dioxane-4-tert-butyl acetate as a raw material, carrying out substitution reaction to prepare a compound (4R-cis)-6-acetoxymethyl-2,2-dimethyl-1,3-dioxane-4-tert-butyl acetate; carrying out a hydrolysis reaction on the compound (4R-cis)-6-acetoxymethyl-2,2-dimethyl-1,3-dioxane-4-tert-butyl acetate to prepare a compound (4R-cis)-6-methylhydroxyl-2,2-dimethyl-1,3-dioxane-4-tert-butyl acetate, and finally carrying out a selective oxidation reaction to obtain the compound (4R-cis)-6-formyl-2,2-dioxane-1,3-dioxane-4-tert-butyl acetate. By adopting a limited method, the problems of low substitution reaction yield and long reaction time in the prior art are solved, and the use of a high-pollution oxidation reagent and the discharge of irritantgas in the oxidation reaction are avoided. The preparation method provided by the invention is green, safe, efficient and suitable for industrial production.

Application of chiral 2-isoxazoline for the synthesis of syn-1,3-diol analogs

The asymmetric cycloaddition of TIPS nitronate catalyzed by “Cu(II)-bisoxazoline” gave the 2-isoxazoline product in 95% yield, which was converted into tert-butyl (3S,5R)-6-hydroxy-3,5-O-isopropylidene-3,5-dihydroxyhexanoate in 14 steps through a β-hydroxy ketone.

Efficient and Practical Deacylation Reaction System in a Continuous Packed-Bed Reactor

The ester deacylation reaction is widely applied in organic synthesis for preparing desired hydroxy compounds, as the acyl group is often used for protecting the hydroxyl group. This reaction is usually performed by acid, base, or enzyme catalysts, which have to be removed by complicated workups such as extraction or filtration in batch mode. Therefore, a simple deacylation process is desirable to improve productivity, especially at the industrial scale. In this work, we established an efficient and practical packed-bed reactor system for undertaking the deacylation reaction using an anion-exchange resin that provides a simple process compared with batch processing. We also demonstrated that this technique is applicable to the preparation of a wide variety of desired pharmaceutical intermediates containing hydroxy groups in good to excellent yields.

Synthesis method of rosuvastatin calcium side chain key intermediate

The invention discloses a synthesis method of a rosuvastatin calcium side chain key intermediate and provides a preparation method of the rosuvastatin calcium side chain key intermediate. (S)-2-(epoxypropane-2-yl)methyl acetate is taken as a starting material and subjected to a condensation reaction, a ring opening reaction, a reduction reaction, a hydroxyl group protecting reaction and a debenzylation reaction. The method is simple and convenient to operate, easy in separation and purification, higher in yield and capable of obtaining the intermediate with higher chemical purity and optical purity.

Preparation method of rosuvastatin calcium medicine intermediate

The invention belongs to the technical field of medicine chemicals, and particularly relates to a preparation method of a rosuvastatin calcium medicine intermediate. The preparation method comprises the following steps of using monochloroacetaldehyde as the raw material; substituting, condensing, and chirally catalyzing, so as to prepare a compound V; protecting by 2,2-dimethoxypropane, and debenzylating, so as to obtain a target compound I. The preparation method has the advantages that the raw materials are easy to obtain; (S)-5-benzyl-2,2,3-trimethyl-4-thioketone is used as a catalyst for stereo selective reduction, the reaction conditions are mild, the yield rate is higher, and the industrialization production of the component I is easy.

A novel process for synthesis of Rosuvastatin

A novel process for the preparation of antihypercholesterolemic drug rosuvastatin calcium using novel intermediates has been described. Novel intermediates have been characterized by using IR, NMR and Mass spectroscopy.

Method for preparing heptenoic acid cyclopentyl ester derivative

The invention discloses a method for preparing a heptenoic acid cyclopentyl ester product by taking (4R-cis)-6-[(acetoxy)methyl]-2,2-dimethyl-1,3-dioxane-4-tert butyl acetate as an initial raw material, and the product is prepared through steps of hydrolysis, replacement and oxidation. The synthesis step is simple, an intermediate can be subjected to a next reaction without refining and purifying steps, for a butt-coupling reaction, the conventional mild technology condition can replace ultralow temperature reaction condition, superbase with high danger is simultaneously replaced, reaction security is increased, the route total yield is high, and the method is suitable for large-scale industrial production.

PROCESSES FOR THE PREPARATION OF ROSUVASTATIN OR PHARMACEUTICALLY ACCEPTABLE SALTS THEREOF

The present invention relates to processes for the preparation of rosuvastatin calcium of formula I and pharmaceutically acceptable salts thereof using novel intermediates, and to a pharmaceutical composition containing the same.