186508-94-1

Basic information

• Product Name: (3S,5R)-6-Cyano-3,5-dihydroxy-hexanoic Acid tert-Butyl Ester
• Synonyms: (3S,5R)-6-Cyano-3,5-dihydroxy-hexanoic Acid tert-Butyl Ester;(3S,5R)-6-Cyano-3,5-dihydroxy-hexanoic Acid 1,1-DiMethylethyl Ester
• CAS NO: 186508-94-1
• Molecular Formula: C₁₁H₁₉NO₄
• Molecular Weight: 229.27286
• Product Categories: Aliphatics;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals;Aliphatics, Chiral Reagents, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 186508-94-1.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 410.244°C at 760 mmHg
• Flash Point: 201.909°C
• Appearance: /
• Density: 1.131g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.48
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform, Ethyl Acetate
• CAS DataBase Reference: (3S,5R)-6-Cyano-3,5-dihydroxy-hexanoic Acid tert-Butyl Ester(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,5R)-6-Cyano-3,5-dihydroxy-hexanoic Acid tert-Butyl Ester(186508-94-1)
• EPA Substance Registry System: (3S,5R)-6-Cyano-3,5-dihydroxy-hexanoic Acid tert-Butyl Ester(186508-94-1)

Safety Data

• Hazardous Substances Data: 186508-94-1(Hazardous Substances Data)

Usage

Description

(3S,5R)-6-Cyano-3,5-dihydroxy-hexanoic Acid tert-Butyl Ester is an organic compound that serves as an intermediate in the synthesis of Atorvastatin 10-Trans (Atorvastatin Impurity AT10). It is characterized by its white solid appearance and specific stereochemistry, with the 3S and 5R configurations contributing to its unique properties.

Uses

Used in Pharmaceutical Industry:
(3S,5R)-6-Cyano-3,5-dihydroxy-hexanoic Acid tert-Butyl Ester is used as a key intermediate in the preparation of Atorvastatin 10-Trans, which is an impurity associated with the production of Atorvastatin. Atorvastatin is a widely prescribed medication for lowering cholesterol levels and managing cardiovascular diseases. The synthesis of this intermediate is crucial for the development and quality control of Atorvastatin, ensuring the safety and efficacy of the final drug product.

InChI:InChI=1/C11H19NO4/c1-11(2,3)16-10(15)7-9(14)6-8(13)4-5-12/h8-9,13-14H,4,6-7H2,1-3H3/t8-,9+/m1/s1

Upstream product

• 125988-01-4 tert-butyl (5R)-6-cyano-5-hydroxy-3-carbonylhexanoate 

Relevant articles and documents

Synthesis of some impurities and/or degradation products of atorvastatin

Synthesis of some impurities and/or degradation products of atorvastatin, calcium (3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl) pyrrol-1-yl]-3,5-dihydroxyheptanoate, is described. These include its desfluoro analog, the corresponding (3S,5S)-and (3S,5R)-epimers, atorvastatin lactone, and some other potential impurities. The synthesized compounds as well as the corresponding intermediates were characterized by 1H NMR, 13C NMR and MS.