(2S,3R,4S,5S,6R)-2-(3-((5-(4-fluorophenyl)thiophen-2-yl)Methyl)-4-Methylphenyl)-tetrahydro-6-(hydroxyMethyl)-2-Methoxy-2H-pyran-3,4,5-triol

Base Information

• Chemical Name: (2S,3R,4S,5S,6R)-2-(3-((5-(4-fluorophenyl)thiophen-2-yl)Methyl)-4-Methylphenyl)-tetrahydro-6-(hydroxyMethyl)-2-Methoxy-2H-pyran-3,4,5-triol
• CAS No.: 1358581-37-9
• Molecular Formula: C25H27FO6S
• Molecular Weight: 474.55
• Mol file: 1358581-37-9.mol

Synonyms:(2S,3R,4S,5S,6R)-2-(3-((5-(4-fluorophenyl)thiophen-2-yl)Methyl)-4-Methylphenyl)-tetrahydro-6-(hydroxyMethyl)-2-Methoxy-2H-pyran-3,4,5-triol;Methyl 1-C-[3-[[5-(4-fluorophenyl)-2-thienyl]methyl]-4-methylphenyl]-alpha-D-glucopyranoside;(2S,3R,4S,5S,6R)-2-[3-[[5-(4-fluorophenyl)-2-thienyl]Methyl]-4-Methyl-phenyl]-6-(hydroxyMethyl)-2-Methoxy-tetrahydropyran-3,4,5-triol

Chemical Property of (2S,3R,4S,5S,6R)-2-(3-((5-(4-fluorophenyl)thiophen-2-yl)Methyl)-4-Methylphenyl)-tetrahydro-6-(hydroxyMethyl)-2-Methoxy-2H-pyran-3,4,5-triol

Chemical Property:

• Boiling Point: 644.5±55.0 °C(Predicted)
• PKA: 12.73±0.70(Predicted)
• PSA: 127.62000
• Density: 1.41±0.1 g/cm3(Predicted)
• LogP: 2.72640

Purity/Quality:

93%, ^*data from raw suppliers

1-MethoxyCanagliflozin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 1-Methoxy Canagliflozin is an impurity in the synthesis of the drug Canagliflozin (C175190). Canagliflozin 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 (2S,3R,4S,5S,6R)-2-(3-((5-(4-fluorophenyl)thiophen-2-yl)Methyl)-4-Methylphenyl)-tetrahydro-6-(hydroxyMethyl)-2-Methoxy-2H-pyran-3,4,5-triol

There total 30 articles about (2S,3R,4S,5S,6R)-2-(3-((5-(4-fluorophenyl)thiophen-2-yl)Methyl)-4-Methylphenyl)-tetrahydro-6-(hydroxyMethyl)-2-Methoxy-2H-pyran-3,4,5-triol 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: 96.6%

methanol (67-56-1) + (2R,3S,4R,5R)-1-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)-2,3,4,5,6-pentahydroxyhexan-1-one → (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 (1358581-37-9)

Guidance literature:

With methanesulfonic acid; Large scale;

Reference yield: 83.0%

methanol (67-56-1) + 3-[[5-(4-fluorophenyl)-2-thienyl]methyl]-4-methylphenyl bromide (1030825-20-7) + (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) → (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 (1358581-37-9)

Guidance literature:

3-[[5-(4-fluorophenyl)-2-thienyl]methyl]-4-methylphenyl bromide; With n-butyllithium; In tetrahydrofuran; hexane; toluene; at -78 ℃; for 1h;

(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one; In tetrahydrofuran; hexane; toluene; at -78 ℃; for 3h;

methanol; With methanesulfonic acid; In tetrahydrofuran; hexane; toluene; at -78 - 40 ℃; for 10h;

Reference yield: 77.8%

3-[[5-(4-fluorophenyl)-2-thienyl]methyl]-4-methylphenyl bromide (1030825-20-7) + C70H82O6Si4 → (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 (1358581-37-9)

Guidance literature:

With sec.-butyllithium; In tetrahydrofuran; hexane; toluene; at -78 - -65 ℃; for 2h; Inert atmosphere;

upstream raw materials:

methanesulfonic acid

(5-bromo-2-chloro-phenyl)-[5-(4-fluorophenyl)-2-thienyl]methanone

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

5-bromo-2-chlorobenzoic acid

Downstream raw materials:

(2S,3R,4S,5S,6R)-6-[(tertbutyl(dimethyl)silyl)oxymethyl]-2-[3-[[5-(4-fluorophenyl)-2-thienyl]methyl]-4-methyl-phenyl]-2-methoxy-tetrahydropyran-3,4,5-triol

[[(2R,3R,4S,5R,6S)-3,4,5-tribenzyloxy-6-[3-[[5-(4-fluorophenyl)-2-thienyl]methyl]-4-methyl-phenyl]-6-methoxy-tetrahydropyran-2-yl]methoxy]tert-butyl-dimethyl-silane

[(2R,3R,4S,5R,6S)-3,4,5-tribenzyloxy-6-[3-[[5-(4-fluorophenyl)-2-thienyl]methyl]-4-methyl-phenyl]-6-methoxy-tetrahydropyran-2-yl]methanol

(2S,3S,4S,5R,6S)-3,4,5-tribenzyloxy-6-[3-[[5-(4-fluorophenyl)-2-thienyl]methyl]-4-methyl-phenyl]-6-methoxy-tetrahydropyran-2-carbaldehyde

Refernces

• 1、 Hone, Christopher A.,Oliver Kappe, C.,Polterauer, Dominik,Williams, Jason D.. "Telescoped lithiation, C-arylation and methoxylation in flow-batch hybrid toward the synthesis of canagliflozin". supporting information. . Retrieved 2021/09/22.
• 2、 -. "Method for preparing intermediates of gliflozin hypoglycemic drugs". . . Retrieved 2020/05/02.