Canagliflozin heMihydrate

Base Information

• Chemical Name: Canagliflozin heMihydrate
• CAS No.: 928672-86-0
• Molecular Formula: C₂₄H₂₅FO₅S*0H₂O
• Molecular Weight: 453.532
• Mol file: 928672-86-0.mol

Synonyms:Canagliflozin hemihydrate;(2S,3R,4R,5S,6R)-2-[3-[[5-(4-fluorophenyl)thiophen-2-yl]methyl]-4-methylphenyl]-6-(hydroxymethyl)oxane-3,4,5-triol,hydrate;TA-7284;UNII-0SAC974Z85;

Chemical Property of Canagliflozin heMihydrate

Chemical Property:

• Appearance/Colour: Light Yellow Solid
• PSA: 246.01000
• Density: 99
• LogP: 5.87230
• Storage Temp.: Hygroscopic, Refrigerator, under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

98% ^*data from raw suppliers

CanagliflozinHemihydrate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: Canagliflozin, an orally active and selective sodium–glucose cotransporter 2 (SGLT2) inhibitor, was co-developed by Mitsubishi Tanabe Pharma and Johnson & Johnson (J&J) for the treatment of type 2 diabetes mellitus (T2DM) and obesity. The drug was approved in March by the U.S. FDA and launched in April 2013 in the U.S. SGLT2 is involved in the glucose re-absorption pathway in the kidney, and its inhibition increases urinary glucose excretion, and reduces plasma glucose and HbA1c levels. In addition, canagliflozin is safe in combination with other commonly used antidiabetic agents and has a significant effect on body weight reduction. A recently published process patent from ScinoPharm Taiwan describes the synthesis of canagliflozin.
• Uses: Canagliflozin Hemihydrate is a derivative of Canagliflozin (C175190), which is a sodium/glucose cotransporter 2 (SGLT2) inhibitor. Canagliflozin has been shown to dose dependently reduce calculated renal threshold for glucose excretion and increase urinary glucose excretion. Canagliflozin is a candidate for the treatment of type 2 diabetes and obesity.

Technology Process of Canagliflozin heMihydrate

There total 3 articles about Canagliflozin heMihydrate 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:

canagliflozin (842133-18-0,1589590-87-3) → 1-(β-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienylmethyl]benzene hydrate (928672-86-0)

Guidance literature:

With water; at 15 - 25 ℃; for 18h; Solvent;

Reference yield:

canagliflozin (842133-18-0,1589590-87-3) → (1S)-1,5-anhydro-1-[3-[[5-(4-fluorophenyl)-2-thienyl]methyl]-4-methylphenyl]-D-glucitol hemihydrate (928672-86-0)

Guidance literature:

With water; In acetone; at 20 ℃; for 18h; Product distribution / selectivity;

Reference yield:

methyl 1-C-(3-{[5-(4-fluorophenyl)-2-thienyl]methyl}-4-methyl-phenyl)-D-glucopyranoside (1030825-21-8) → (1S)-1,5-anhydro-1-[3-[[5-(4-fluorophenyl)-2-thienyl]methyl]-4-methylphenyl]-D-glucitol hemihydrate (928672-86-0)

Guidance literature:

methyl 1-C-(3-{[5-(4-fluorophenyl)-2-thienyl]methyl}-4-methyl-phenyl)-D-glucopyranoside; With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; at 0 ℃; for 2h; Cooling with acetone-dry ice;

With water; sodium hydrogencarbonate; In dichloromethane; for 0.5h; Product distribution / selectivity;

upstream raw materials:

canagliflozin

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

Refernces

• 1、 -. "Crystalline form of 1-(beta-D-glucopyransoyl)-4-methyl-3-[5-(4-fluorophenyl)-2- thienylmethyl]benzene hemihydrate". Page/Page column 4. . Retrieved 2008/12/06.