842133-16-8

Basic information

• Product Name: D-Glucitol, 1,5-anhydro-1-C-[4-Methyl-3-[(5-phenyl-2-thienyl)Methyl]phenyl]-, (1S)-
• Synonyms: D-Glucitol, 1,5-anhydro-1-C-[4-Methyl-3-[(5-phenyl-2-thienyl)Methyl]phenyl]-, (1S)-;Canagliflozin Impurity A;Defluoro-Canagliflozin
• CAS NO: 842133-16-8
• Molecular Formula: C24H26O5S
• Molecular Weight: 426.52524
• Mol File: 842133-16-8.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 645.1±55.0 °C(Predicted)
• Appearance: /
• Density: 1.326±0.06 g/cm3(Predicted)
• PKA: 13.34±0.70(Predicted)
• CAS DataBase Reference: D-Glucitol, 1,5-anhydro-1-C-[4-Methyl-3-[(5-phenyl-2-thienyl)Methyl]phenyl]-, (1S)-(CAS DataBase Reference)
• NIST Chemistry Reference: D-Glucitol, 1,5-anhydro-1-C-[4-Methyl-3-[(5-phenyl-2-thienyl)Methyl]phenyl]-, (1S)-(842133-16-8)
• EPA Substance Registry System: D-Glucitol, 1,5-anhydro-1-C-[4-Methyl-3-[(5-phenyl-2-thienyl)Methyl]phenyl]-, (1S)-(842133-16-8)

Safety Data

• Hazardous Substances Data: 842133-16-8(Hazardous Substances Data)

Usage

Description

D-Glucitol, 1,5-anhydro-1-C-[4-Methyl-3-[(5-phenyl-2-thienyl)Methyl]phenyl]-, (1S)is a complex organic compound with a unique molecular structure. It is an impurity of Canagliflozin, a sodium/glucose cotransporter 2 (SGLT2) inhibitor, which has potential applications in the treatment of type 2 diabetes and obesity.

Uses

Used in Pharmaceutical Industry:
D-Glucitol, 1,5-anhydro-1-C-[4-Methyl-3-[(5-phenyl-2-thienyl)Methyl]phenyl]-, (1S)is used as an impurity in Canagliflozin, a drug candidate for the treatment of type 2 diabetes and obesity. Canagliflozin has been shown to dose-dependently reduce the calculated renal threshold for glucose excretion and increase urinary glucose excretion, making it a promising therapeutic option for these conditions.

Upstream product

• 1089333-87-8 2-(4-fluorophenyl)-5-methylthiophene 
• 765-58-2 2-bromo-5-methyl thiophene 
• 1765-93-1 4-fluoroboronic acid 
• 90-80-2 D-Glucono-1,5-lactone 
• 32469-28-6 (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one 

Relevant articles and documents

Synthesis method of canagliflozin

The invention relates to a synthesis method of canagliflozin. According to the synthesis method, 4-fluorophenylboronic acid is taken as an initial raw material to be coupled with 2-methyl-5-bromo-thiophene to synthesize 2-methyl-5-(4-fluorophenyl)thiophene, the 2-methyl-5-(4-fluorophenyl)thiophene undergoes bromation and then undergoes Friedel-Crafts alkylation reaction with 4-bromotoluene to synthesize 2-(2-methyl-5-bromobenzyl)-5-(4-fluorophenyl)thiophene, and the 2-(2-methyl-5-bromobenzyl)-5-(4-fluorophenyl)thiophene undergoes condensation, etherification and methoxyl removal with 2,3,4,6-tetra-O-trimethylsilyl-D-gluconolactone to obtain the hypoglycemic drug canagliflozin. The synthesis method has the following advantages: compared with the conventional synthesis methods, the synthesisprocess takes the 4-fluorobenzeneboronic acid as an initial raw material, so that the raw material is cheap and easy to get, the process is easy to realize industrialization, the synthesis route is short and the operation is easy; in the synthesis process, bromine is not used or butyl lithium does not need to be used twice, so that the risk of the process can be reduced; in addition, the synthesis method is capable of improving the yield of canagliflozin products to 70% or more.