Ethyl (R)-(-)-4-cyano-3-hydroxybutyate

Ethyl (R)-(-)-4-cyano-3-hydroxybutyate

Product Introduction

Ethyl (R)-(-)-4-cyano-3-hydroxybutyate Basic information
Product Name: Ethyl (R)-(-)-4-cyano-3-hydroxybutyate
Synonyms: (R)-(-)-4-CYANO-3-HYDROXYBUTYRIC ACID ETHYL ESTER;(R)-4-CYANO-3-HYDROXYBUTYRIC ACID ETHYL ESTER;(R)-(-)-ETHYL 4-CYANO-3-HYDROXYBUTYRATE;(R)-ETHYL 4-CYANO-3-HYDROXYBUTYRATE;(S)-4-CYANO-3-HYDROXYBUTANOATE ETHYL;ETHYL (3R)-4-CYANO-3-HYDROXY-BUTANOATE;ETHYL (S)-4-CYANO-3-HYDROXYBUTANOATE;ETHYL (R)-4-CYANO-3-HYDROXYBUTANOATE
CAS: 141942-85-0
MF: C7H11NO3
MW: 157.17
EINECS: 430-220-6
Product Categories: Atorvastatin intermediates;chiral;Alcohols, Hydroxy Esters and Derivatives;Chiral Compounds;INTERMEDIATESOFATORVASTATIN;API intermediates;Pharmaceutical Intermediates;141942-85-0
Mol File: 141942-85-0.mol
Ethyl (R)-(-)-4-cyano-3-hydroxybutyate Structure
 
Ethyl (R)-(-)-4-cyano-3-hydroxybutyate Chemical Properties
alpha -5 º (neat)
Boiling point 270 °C(lit.)
density 1.114 g/mL at 25 °C(lit.)
refractive index n20/D 1.448(lit.)
Fp >230 °F
storage temp. 2-8°C
solubility Chloroform (Sparingly), DMSO (Slightly), Methanol (Slightly)
pka 13.03±0.20(Predicted)
form Liquid
Specific Gravity 1.114
color Colorless to yellow
optical activity [α]25/D 5°, neat
BRN 5328715
InChIKey LOQFROBMBSKWQY-ZCFIWIBFSA-N
CAS DataBase Reference 141942-85-0(CAS DataBase Reference)
 
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-36
WGK Germany 1
HS Code 29269090
 
MSDS Information
Provider Language
SigmaAldrich English
ALFA English
 
Ethyl (R)-(-)-4-cyano-3-hydroxybutyate Usage And Synthesis
Chemical Properties yellow liquid
Uses analgesic, antipyretic, and anti-inflammatory
Uses (3R)-4-Cyano-3-hydroxybutanoic Acid Ethyl Ester is used in a biocatalytic process for the synthesis of an atorvastatin intermediate and degredation products/impurities.
Application Hydroxyglutaryl coenzyme A (HMG-CoA) reductase inhibitors are a new class of lipid-lowering drugs, and they have a market share of more than 10 billion US dollars in the current pharmaceutical field. They can selectively inhibit the rate-limiting enzyme HMG-CoA reductase in cholesterol synthesis in the liver, reduce liver lipoprotein production, and increase the expression of low-density lipoprotein (LDL) cholesterol receptors, thereby reducing plasma cholesterol levels. They can also significantly reduce very low-density lipoprotein (VLDL) and triglycerides, and increase anti-atherosclerotic high-density protein (HDL), preventing atherosclerosis and coronary heart disease.
Ethyl (R)-(-)-4-cyano-3-hydroxybutyate is an important intermediate for the synthesis of HMG-CoA reductase inhibitors. If it is used as a raw material, synthetic atorvastatin is mainly used for the treatment of hypercholesterolemia and mixed hyperlipidemia, coronary heart disease and stroke.
 
Ethyl (R)-(-)-4-cyano-3-hydroxybutyate Preparation Products And Raw materials
Raw materials Butanoic acid, 4-cyano-3-hydroxy-, (3R)--->Ethyl 4-bromo-3-hydroxybutyrate-->Sodium cyanide-->Ethanol-->Ethyl 4-chloroacetoacetate
Preparation Products (3R,5R)-6-Cyano-3,5-dihydroxy-hexanoic Acid tert-Butyl Ester

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