125971-94-0

Basic information

• Product Name: (4R,6R)-tert-Butyl-6-cyanomethyl-2,2-dimethyl-1,3-dioxane-4-acetate
• Synonyms: ATS-8;(4R,6R)-T-BUTYL-6-CYANOMETHYL-2,2-DIMETHYL-1,3-DIOXANE-4-ACETATE;(4R,6R)-TERT-BUTYL-6-CYANOMETHYL-2,2-DIMETHYL-1,3-DIOXANE-4-ACETATE;(4R,CIS)-1,1-DIMETHYLETHYL-6-CYANOMETHYL-2,2-DIMETHYL-1,3-DIOXANE-4-ACETATE;(4R,3R)-TERT-BUTYL-6-CYANOMETHYL-2,2-DIMETHYL-1,3-DIOXANE-4-ACETATE;tert-Butyl (4R,3R)-6-cyanomethyl-2,2-dimethyl-1,3-dioxane-4-acetate;TERT-BUTYL[(4R,6R)-6-CYANOMETHYL-2,2-DIMETHYL-1,3-DIOXAN-4-YL]ACETATE;(4R-CIS)-1,1-DIMETHYLETHYL-6-CYANOMETHYL-2,2-DIMETHYL-1,3-DIOXANE-4-ACETATE (ATS-8)
• CAS NO: 125971-94-0
• Molecular Formula: C₁₄H₂₃NO₄
• Molecular Weight: 269.34
• EINECS: 425-780-3
• Product Categories: Chemical intermediate for Atorvastatin Calcium;INTERMEDIATESOFATORVASTATIN;chiral;(intermediate of atorvastatin);Chiral Building Blocks;Cyanides/Nitriles;Organic Building Blocks;Atorvastatin intermediates
• Mol File: 125971-94-0.mol
• Article Data: 13

Chemical Properties

• Melting Point: 65-69 °C(lit.)
• Boiling Point: 364.1 °C at 760 mmHg
• Flash Point: 159.2 °C
• Appearance: white to light yellow crystal powder
• Density: 1.016 g/cm³
• Vapor Pressure: 1.73E-05mmHg at 25°C
• Refractive Index: 1.439
• Storage Temp.: 2-8°C
• Solubility: soluble in Chloroform
• CAS DataBase Reference: (4R,6R)-tert-Butyl-6-cyanomethyl-2,2-dimethyl-1,3-dioxane-4-acetate(CAS DataBase Reference)
• NIST Chemistry Reference: (4R,6R)-tert-Butyl-6-cyanomethyl-2,2-dimethyl-1,3-dioxane-4-acetate(125971-94-0)
• EPA Substance Registry System: (4R,6R)-tert-Butyl-6-cyanomethyl-2,2-dimethyl-1,3-dioxane-4-acetate(125971-94-0)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 125971-94-0(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powde

Uses

Different sources of media describe the Uses of 125971-94-0 differently. You can refer to the following data:
1. Atorvastatin Intermediate
2. (4R,6R)-6-(Cyanomethyl)-2,2-dimethyl-1,3-dioxane-4-acetic Acid 1,1-Dimethylethyl Ester is an intermediate of Atorvastatin (A791750, Ca salt), a selective, competitive HMG-CoA reductase . Atorvastatin is the only drug in its class specfically indicated for lowering both elevated LDL-cholesterol and triglyceinhibitorrides in patients with hypercholesterolemia.

InChI:InChI=1/C14H23NO4/c1-13(2,3)19-12(16)9-11-8-10(6-7-15)17-14(4,5)18-11/h10-11H,6,8-9H2,1-5H3/t10-,11-/m1/s1

Upstream product

• 125971-93-9 (3R,5R)-tert-butyl-6-cyano-3,5-dihydroxyhexanoate 
• 74530-57-7 tert-butyl 4-bromoacetoacetate 
• 154026-94-5 (4R-cis)-6-(chloromethyl)-2,2-dimethyl-1,3-dioxane-4-acetic acid,1,1-dimethylethyl ester 
• 848644-99-5 (5R)-1,1-dimethylethyl 6-cyano-5-hydroxy-3-oxo-hexanoate 
• 7397-46-8 diethyl methoxy borane 
• 791115-48-5 ((4R,6R)-6-cyanomethyl-2,2-dimethyl-[1,3]-dioxan-4-yl)-acetic acid chloride 
• 75-65-0 tert-butyl alcohol 
• 773837-37-9 sodium cyanide 
• 125971-92-8 (R)-1,1-dimethylethyl 6-cyano-5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3oxohexanoate 
• 477541-55-2 (R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-imidazol-1-yl-5-oxo-pentanenitrile 
• 141942-83-8 (R)-3-(tert-Butyl-dimethyl-silanyloxy)-4-cyano-butyric acid butyl ester 
• 141942-82-7 (R)-(-)-ethyl 4-cyano-3-(tert-butyldimethylsilyloxy)butyrate 
• 105876-27-5 (R)-4-cyano-3-hydroxybutanoic acid methyl ester 
• 125988-01-4 tert-butyl (5R)-6-cyano-5-hydroxy-3-carbonylhexanoate 

Downstream Products

• 134523-01-6 atorvastatin sodium 
• 134395-00-9 (3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester 
• 125971-95-1 tert-butyl (4R,6R)-6-{2-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)pyrrol-1-yl]ethyl}-2,2-dimethyl-1,3-dioxane-4-acetate 
• 134523-03-8 lipitor 
• 125971-86-0 tert-butyl [(4R,6R)-6-aminoethyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate 

Relevant articles and documents

Atorvastatin calcium intermediate as well as preparation method and application thereof

The invention discloses an atorvastatin calcium intermediate as well as a preparation method and application thereof. A synthesis process of the intermediate is environmentally-friendly, simple to operate and low in EHS risk; raw materials are easy to obtain; a used chemical reagent is small in toxicity and low in cost; and the synthesis process is a green synthesis process suitable for the industrial production. Moreover, the intermediate provided by the invention is applied to the synthesis of atorvastatin calcium and a key intermediate thereof, the route is relatively short, the yield is high, the industrial production cost of the atorvastatin calcium is effectively reduced, and the atorvastatin calcium intermediate has a relatively high industrial application prospect.

Preparation method of atorvastatin calcium intermediate

The invention belongs to the field of medicines and chemical industry, and particularly relates to the field of pharmacy, in particular to a preparation method of an atorvastatin calcium intermediate.The preparation method comprises the following steps: firstly preparing a compound II into a lithium reagent, then reacting with methyl chloroformate, introducing an ester group, aminolyzing the ester group into amine, dehydrating the amide, and finally reducing a cyano group to obtain a target compound. By the brand-new preparation method of the atorvastatin calcium intermediate, a compound VI can be synthesized under the premise that highly toxic substances such as hydrocyanic acid, hydrobromide and the like are not used, and the compound VI is used for preparing a compound I; reagents usedin the whole preparation process are safe and environment-friendly, and the preparation method is more suitable for industrial production.

2 - ((4R, 6R) - 6-aminomethyl-ethyl -2,2-dimethyl -1,3-dioxane-4-yl) acetate simple method for preparing

The invention relates to a simple preparation method of 2-((4R,6R)-6-aminoethyl-2,2-dimethyl-1,3-dioxyhexacyclo-4-yl)acetate (I). The method comprises the following steps: reacting 3-cyanopropylene (II) and 3,3-dialkoxypropionate (III) or 3-alkoxyacrylate (IV) under the catalytic action of Lewis acid to prepare 2-((4R,6R)-6-cyanomethyl-2-ester-methyl-1,3-dioxyhexacyclo-4-yl)acetate (V), removing the solvent, directly carrying out blocking group conversion to prepare 2-((4R,6R)-6-cyanomethyl-2,2-dimethyl-1,3-dioxyhexacyclo-4-yl)acetate (VI), and carrying out Raney nickel catalytic hydrogenation two-step reaction to prepare (I). The stable form of the hexatomic ring chair-structure equatorial bond is utilized to construct the chiral center without using any additional chiral assistant. The method has the advantages of accessible raw materials, short reaction procedure and low cost, avoids carbonyl asymmetric reduction, is simple and environment-friendly, and is industrial production.