1620758-34-0

Basic information

• Product Name: (3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxyMethyl)tetrahydro-2H-pyran-2,3,4,5-tetraol
• Synonyms: Empagliflozin impurity I;(3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxyMethyl)tetrahydro-2H-pyran-2,3,4,5-tetraol;EMpagliflozin iMpurity 4;Jardiance Impurity E;Empagliflozin Impurity A -D;(1R)-1,5-Dihydroxyempagliflozin
• CAS NO: 1620758-34-0
• Molecular Formula: C23H27ClO8
• Molecular Weight: 466.90868
• EINECS: -0
• Mol File: 1620758-34-0.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 770.5±60.0 °C(Predicted)
• Appearance: /
• Density: 1.435±0.06 g/cm3(Predicted)
• PKA: 13.25±0.20(Predicted)
• CAS DataBase Reference: (3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxyMethyl)tetrahydro-2H-pyran-2,3,4,5-tetraol(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxyMethyl)tetrahydro-2H-pyran-2,3,4,5-tetraol(1620758-34-0)
• EPA Substance Registry System: (3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxyMethyl)tetrahydro-2H-pyran-2,3,4,5-tetraol(1620758-34-0)

Safety Data

• Hazardous Substances Data: 1620758-34-0(Hazardous Substances Data)

Usage

Uses

(1R)-1,5,-Dihydroxyempagliflozin is an impurity of Empagliflozin (E521510) which is a novel, potent and selective SGLT-2 inhibitor, improves glycaemic control and features of metabolic syndrome in diabetic rats.

Upstream product

• 915095-86-2 (2-chloro-5-iodophenyl)(4-fluorophenyl)methanone 
• 281652-58-2 2-chloro-5-iodobenzoylchloride 
• 19094-56-5 2-chloro-5-iodobenzoic acid 
• 915095-94-2 (3S)-3-[4-[(2-chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran 
• 32469-28-6 (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one 
• 915095-87-3 (S)-(2-chloro-5-iodophenyl)(4-((tetrahydrofuran-3-yl)oxy)phenyl)methanone 

Relevant articles and documents

Efficient synthesis of empagliflozin, an inhibitor of SGLT-2, utilizing an AlCl3-promoted silane reduction of a β-glycopyranoside

An efficient production synthesis of the SGLT-2 inhibitor Empagliflozin (5) from acid 1 is described. The key tactical stage involves I/Mg exchange of aryl iodide 2 followed by addition to glucono lactone 3 in THF. Subsequent in situ treatment of the resulting lactol with HCl in MeOH produces β-anomeric methyl glycopyranoside 4 which is, without isolation, directly reduced with Et3SiH mediated by AlCl3 as a Lewis acid in CH 2Cl2/MeCN to afford 5 in 50% overall yield. The process was implemented for production on a metric ton scale for commercial launch.