D-Glucitol, 1,5-anhydro-1-C-[4-Methyl-3-[(5-phenyl-2-thienyl)Methyl]phenyl]-, (1S)-

Base Information

• Chemical Name: D-Glucitol, 1,5-anhydro-1-C-[4-Methyl-3-[(5-phenyl-2-thienyl)Methyl]phenyl]-, (1S)-
• CAS No.: 842133-16-8
• Molecular Formula: C₂₄H₂₆O₅S
• Molecular Weight: 426.533
• Mol file: 842133-16-8.mol

Synonyms:D-Glucitol, 1,5-anhydro-1-C-[4-Methyl-3-[(5-phenyl-2-thienyl)Methyl]phenyl]-, (1S)-;Canagliflozin Impurity A

Chemical Property of D-Glucitol, 1,5-anhydro-1-C-[4-Methyl-3-[(5-phenyl-2-thienyl)Methyl]phenyl]-, (1S)-

Chemical Property:

• Boiling Point: 645.1±55.0 °C(Predicted)
• PKA: 13.34±0.70(Predicted)
• PSA: 118.39000
• Density: 1.326±0.06 g/cm3(Predicted)
• LogP: 2.82920

Purity/Quality:

> 95% ^*data from raw suppliers

Defluoro-Canagliflozin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: Defluoro-Canagliflozin is an impurity of Canagliflozin (C175190), 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 D-Glucitol, 1,5-anhydro-1-C-[4-Methyl-3-[(5-phenyl-2-thienyl)Methyl]phenyl]-, (1S)-

There total 10 articles about D-Glucitol, 1,5-anhydro-1-C-[4-Methyl-3-[(5-phenyl-2-thienyl)Methyl]phenyl]-, (1S)- 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: 74.0%

C25H28O6S → defluoro-canagliflozin (842133-16-8)

Guidance literature:

C₂₅H₂₈O₆S; With aluminum (III) chloride; In dichloromethane; acetonitrile; for 0.5h;

With triethylsilane; In dichloromethane; acetonitrile; at 10 ℃; for 2h;

Reference yield: 61.0%

C32H34O9S → defluoro-canagliflozin (842133-16-8)

Guidance literature:

C₃₂H₃₄O₉S; With sodium methylate; In methanol; at 0 - 25 ℃; for 2h;

With pyrographite; acetic acid; In methanol; at 15 - 20 ℃; for 0.5h;

Reference yield:

(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one (32469-28-6,55515-28-1,55515-29-2,32384-65-9) → defluoro-canagliflozin (842133-16-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: isopropylmagnesium chloride; lithium chloride / toluene; tetrahydrofuran / 4 h / -25 - -15 °C / Autoclave; Inert atmosphere

1.2: 3 h / -20 - -15 °C / Inert atmosphere

2.1: 4-methyl-morpholine; dmap / toluene / 5 h / 5 - 25 °C

3.1: triethylsilane / tetrahydrofuran; acetonitrile / 3 h / -15 - 25 °C / Autoclave

4.1: sodium methylate / methanol / 2 h / 0 - 25 °C

4.2: 0.5 h / 15 - 20 °C

With 4-methyl-morpholine; triethylsilane; dmap; isopropylmagnesium chloride; sodium methylate; lithium chloride; In tetrahydrofuran; methanol; toluene; acetonitrile;

upstream raw materials:

(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one

D-Glucono-1,5-lactone

4-fluoroboronic acid

2-bromo-5-methyl thiophene