407577-54-2

Basic information

• Product Name: (4R,6R)-6-HydroxyMethyl-2,2-diMethyl-1,3-dioxane-4-acetic Acid 1,1-DiMethylethyl Ester
• Synonyms: (4R,6R)-6-HydroxyMethyl-2,2-diMethyl-1,3-dioxane-4-acetic Acid 1,1-DiMethylethyl Ester;2,4-Dideoxy-3,5-O-(1-Methylethylidene)-L-threo-Hexonic Acid 1,1-DiMethylethyl Ester
• CAS NO: 407577-54-2
• Molecular Formula: C13H24O5
• Molecular Weight: 260.32666
• Product Categories: Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals;Chiral Reagents, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 407577-54-2.mol
• Article Data: 30

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (4R,6R)-6-HydroxyMethyl-2,2-diMethyl-1,3-dioxane-4-acetic Acid 1,1-DiMethylethyl Ester(CAS DataBase Reference)
• NIST Chemistry Reference: (4R,6R)-6-HydroxyMethyl-2,2-diMethyl-1,3-dioxane-4-acetic Acid 1,1-DiMethylethyl Ester(407577-54-2)
• EPA Substance Registry System: (4R,6R)-6-HydroxyMethyl-2,2-diMethyl-1,3-dioxane-4-acetic Acid 1,1-DiMethylethyl Ester(407577-54-2)

Safety Data

• Hazardous Substances Data: 407577-54-2(Hazardous Substances Data)

Usage

Description

(4R,6R)-6-HydroxyMethyl-2,2-diMethyl-1,3-dioxane-4-acetic Acid 1,1-DiMethylethyl Ester is a complex organic compound characterized by its unique stereochemistry and structural features. It is a synthetic intermediate with significant importance in the pharmaceutical industry due to its role in the preparation of specific drug molecules.

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

• 140387-94-6 1-methyl 6-tert.-butyl (2S,4R)-2,4-O-isopropylidene-2,4-dihydroxyadipate 
• 154026-94-5 (4R-cis)-6-(chloromethyl)-2,2-dimethyl-1,3-dioxane-4-acetic acid,1,1-dimethylethyl ester 
• 521973-99-9 (4R-cis)-6-chloromethyl-2,2-dimethyl-1,3-dioxane-4-acetic acid tert-butyl ester 
• 1044518-94-6 tert-butyl 2-((4S,6R)-6-[(tert-butyl)dimethylsilyloxymethyl]-2,2-dimethyl-1,3-dioxan-4-yl)acetate 
• 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 
• 147849-64-7 tert-butyl (S)-6-(benzyloxy)-5-hydroxy-3-oxohexanoate 
• 623566-51-8 tert-butyl (S)-4-(propylene oxide-2-yl)-3-oxobutanoate 
• 154026-93-4 1,1-dimethylethyl (3R,5S)-6-chloro-3,5-dihydroxy-4-hexanoate 
• 154026-92-3 Tert-butyl (5S)-6-chloro-5-hydroxy-3-oxohexanoate 
• 521973-99-9 tert-butyl 2-((6S)-6-(chloromethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate 
• 406680-96-4 tert-butyl (5S)-6-chloro-3,5-dihydroxyhexanoate 
• 1067638-10-1 C₁₈H₃₂O₆ 
• 154026-95-6 (4R-cis)-6-[(acetyloxy)methyl]-2,2-dimethyl-1,3-dioxane-4-acetic acid tert-butyl ester 

Downstream Products

• 1044518-75-3 (4R-cis)-6-formyl-2,2-dimethyl-1,3-dioxane-4-acetic acid tert-butyl ester 
• 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 
• 132895-33-1 (4S,6S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-4-hydroxy-tetrahydro-pyran-2-one 
• 132895-31-9 (4R,6S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-4-hydroxy-tetrahydro-pyran-2-one 
• 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 articles and documents

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.

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.

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.