1589590-87-3

Basic information

• Product Name: Canagliflozin α Isomer
• Synonyms: Canagliflozin α Isomer;Canagliflozin Impurity C
• CAS NO: 1589590-87-3
• Molecular Formula: C24H25FO5S
• Molecular Weight: 444.5157032
• EINECS: -0
• Product Categories: Impurities
• Mol File: 1589590-87-3.mol
• Article Data: 49

Chemical Properties

• Boiling Point: 642.9±55.0 °C(Predicted)
• Appearance: /
• Density: 1.364±0.06 g/cm3(Predicted)
• PKA: 13.34±0.70(Predicted)
• CAS DataBase Reference: Canagliflozin α Isomer(CAS DataBase Reference)
• NIST Chemistry Reference: Canagliflozin α Isomer(1589590-87-3)
• EPA Substance Registry System: Canagliflozin α Isomer(1589590-87-3)

Safety Data

• Hazardous Substances Data: 1589590-87-3(Hazardous Substances Data)

Usage

Uses

epi-Canagliflozin is an epimeric impurity of Canagliflozin which is a sodium/glucose cotransporter 2 (SGLT2) inhibitor and is used in the treatment of type 2 diabetes and obesity.

Upstream product

• 1132832-76-8 1-[1-hydroxy-2,3,4,6-tetra-O-(trimethylsilyl)-β-D-glucopyranosyl]-4-methyl-3-[[5-(4-fluorophenyl)-2-thienyl]methyl]benzene 
• 866607-35-4 (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 1030825-21-8 methyl 1-C-(3-{[5-(4-fluorophenyl)-2-thienyl]methyl}-4-methyl-phenyl)-D-glucopyranoside 
• 1358581-37-9 (2S,3R,4S,5S,6R)-2-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)-6-(hydroxylmethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol 
• 1198-69-2 D-glucono-1,4-lactone 
• 604-68-2 α-D-glucopyranose peracetylate 
• 604-69-3 β-D-glucose pentaacetate 
• 4451-35-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl chloride 
• 1335-57-5 3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-one 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 13096-62-3 (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one 

Downstream Products

• 928672-86-0 1-(β-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienylmethyl]benzene hydrate 
• 1951467-29-0 [2-methyl-5-(β-D-glucopyranosyl)phenyl][5-(4-fluorophenyl)-2-thienyl]methanol 
• 1432187-87-5 canagliflozin L-phenylalanine complex 
• 1432187-89-7 canagliflozin D-proline complex 
• 1409936-69-1 (2S,3R,4R,5S,6R)-2-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol citric acid co-crystal 

Relevant articles and documents

Stereoselective Preparation of C-Aryl Glycosides via Visible-Light-Induced Nickel-Catalyzed Reductive Cross-Coupling of Glycosyl Chlorides and Aryl Bromides

A nickel-catalyzed cross-coupling reaction of glycosyl chlorides with aryl bromides has been developed. The reaction proceeds smoothly under visible-light irradiation and features the use of bench-stable glycosyl chlorides, allowing the highly stereoselective synthesis of C-aryl glycosides. (Figure presented.).

Preparation method of SGLT-2 inhibitor and intermediate

The invention discloses a preparation method of an SGLT-2 inhibitor and an intermediate. The method comprises the following steps: (1) reacting a compound A with chlorosilane under the action of an acid-binding agent to generate a compound B; (2) mixing the compound B and a compound C to obtain a compound D; and (3) reacting the compound D with a reducing agent and a catalyst to obtain the SGLT-2 inhibitor compound.

Preparation method of canagliflozin

The invention discloses a preparation method of canagliflozin. According to the method, the reaction of each step in a route is improved, so that the conversion rate of raw materials is increased, andintroduction of potential toxic compounds is avoided. In addition, reaction conditions are mild; operation is simple; purity of an obtained product is high; quality of drugs is improved; and the preparation method is suitable for industrial production.