Canagliflozin α Isomer

Base Information

• Chemical Name: Canagliflozin α Isomer
• CAS No.: 1589590-87-3
• Molecular Formula: C24H25FO5S
• Molecular Weight: 444.52
• Mol file: 1589590-87-3.mol

Synonyms:Canagliflozin α Isomer;Canagliflozin Impurity C

Chemical Property of Canagliflozin α Isomer

Chemical Property:

• Boiling Point: 642.9±55.0 °C(Predicted)
• PKA: 13.34±0.70(Predicted)
• PSA: 118.39000
• Density: 1.364±0.06 g/cm3(Predicted)
• LogP: 2.96830

Purity/Quality:

NLT 98% ^*data from raw suppliers

epi-Canagliflozin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• 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.

Technology Process of Canagliflozin α Isomer

There total 87 articles about Canagliflozin α Isomer which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

(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 (866607-35-4) → canagliflozin (842133-18-0,1589590-87-3)

Guidance literature:

With methanol; sodium methylate; at 20 ℃; for 12h; Sealed tube;

DOI:10.1002/adsc.202100343

Reference yield: 96.0%

(2S,3S,4R,5R,6R)-6-(benzoylmethyl)-3,4,5-tribenzoyl-2-{3-[(5-(4-fluorophenyl)-2-thienyl)methyl]-4-methylphenyl}-2H-glucopyranoside → canagliflozin (842133-18-0,1589590-87-3)

Guidance literature:

With sodium methylate; In tetrahydrofuran; methanol; at 40 ℃; for 2h;

Reference yield: 93.3%

C44H45Cl12FO9S → canagliflozin (842133-18-0,1589590-87-3)

Guidance literature:

With water; lithium hydroxide; In methanol; at 0 - 5 ℃; for 16h;

upstream raw materials:

1-[1-hydroxy-2,3,4,6-tetra-O-(trimethylsilyl)-β-D-glucopyranosyl]-4-methyl-3-[[5-(4-fluorophenyl)-2-thienyl]methyl]benzene

(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

methyl 1-C-(3-{[5-(4-fluorophenyl)-2-thienyl]methyl}-4-methyl-phenyl)-D-glucopyranoside

(2S,3S,4R,5R,6R)-2-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)-6-(pivaloyloxymethyl)tetrahydro-2H-pyran-3,4,5-triyl tris(2,2-dimethylpropanoate)

Downstream raw materials:

[2-methyl-5-(β-D-glucopyranosyl)phenyl][5-(4-fluorophenyl)-2-thienyl]methanol

1-(β-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienylmethyl]benzene hydrate

canagliflozin L-phenylalanine complex

canagliflozin D-proline complex

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