Canagliflozin supplier | CasNO.842133-18-0

Name
Canagliflozin
EINECS 695-192-1
CAS No. 842133-18-0
Article Data45
CAS DataBase
Density 1.4±0.1 g/cm³
Solubility
Melting Point
Formula C₂₄H₂₅FO₅S
Boiling Point 642.9±55.0 °C at 760 mmHg
Molecular Weight 444.524
Flash Point 342.6±31.5 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms (1S)-1,5-Anhydro-1-(3-{[5-(4-fluorophenyl)-2-thienyl]methyl}-4-methylphenyl)-D-glucitol;
PSA 118.39000
LogP 2.96830

Synthetic route

: 866607-35-4
(3R,4R,5S)-2-(acetoxymethyl)-6-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

: 842133-18-0
canagliflozin

Conditions

Conditions	Yield
With water; sodium hydroxide In tetrahydrofuran; methanol at 20 - 25℃; for 1.16667h;	98%
With di(n-butyl)tin oxide In methanol for 24h; Reflux; Inert atmosphere;	95%
With methanol; sodium methylate In tetrahydrofuran at 0 - 10℃; for 3h; Reagent/catalyst;	94.9%

: (2S,3S,4R,5R,6R)-6-(benzoylmethyl)-3,4,5-tribenzoyl-2-{3-[(5-(4-fluorophenyl)-2-thienyl)methyl]-4-methylphenyl}-2H-glucopyranoside

: 842133-18-0
canagliflozin

Conditions

Conditions	Yield
With sodium methylate In tetrahydrofuran; methanol at 40℃; for 2h;	96%

: C44H45Cl12FO9S

: 842133-18-0
canagliflozin

Conditions

Conditions	Yield
With water; lithium hydroxide In methanol at 0 - 5℃; for 16h;	93.3%

: C44H49Cl8FO9S

: 842133-18-0
canagliflozin

Conditions

Conditions	Yield
With water; lithium hydroxide In methanol at 0 - 5℃; for 16h;	92.1%

: C44H53Cl4FO9S

: 842133-18-0
canagliflozin

Conditions

Conditions	Yield
With water; potassium hydroxide In tetrahydrofuran; methanol at 0 - 5℃; for 16h; Reagent/catalyst; Solvent;	92.1%

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

: 842133-18-0
canagliflozin

Conditions

Conditions	Yield
With trimethylsilyl iodide In dichloromethane at 0 - 20℃; for 8h; Inert atmosphere; Schlenk technique; Glovebox;	92%
With palladium 10% on activated carbon In dichloromethane Inert atmosphere;	90%
With trimethylsilyl iodide In dichloromethane at 0 - 30℃; Concentration; Reagent/catalyst; Temperature; Solvent;	90%

: 1283129-18-9
(2S,3S,4R,5R,6R)-2-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)-6-(pivaloyloxymethyl)tetrahydro-2H-pyran-3,4,5-thiyl tris(2,2-dimethylpropanoate)

: 842133-18-0
canagliflozin

Conditions

Conditions	Yield
With hydrogenchloride In methanol; water for 2h; Reflux; Large scale;	91%
With methanol; sodium methylate at 60℃; for 16h; Product distribution / selectivity;	90%
Multi-step reaction with 2 steps 1: methanol / 16 h / 20 - 60 °C 2: water / 1 h / 0 °C View Scheme

: 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

: 842133-18-0
canagliflozin

Conditions

Conditions	Yield
With triethylsilane; boron trifluoride diethyl etherate In dichloromethane at -40 - 0℃; for 3h;	90%
Stage #1: (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 With aluminum (III) chloride In dichloromethane; acetonitrile at -5℃; for 0.5h; Stage #2: With triethylsilane In dichloromethane; acetonitrile at -5 - 10℃; for 2h;	79%
With triethylsilane; acetonitrile boron trifluoride complex In n-heptane at -5 - 5℃; for 5h;	77.5%

: C44H57FO9S

: 842133-18-0
canagliflozin

Conditions

Conditions	Yield
With methanol Temperature;	85%

: 1030825-21-8
(3R,4S,5S,6R)-2-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

: 842133-18-0
canagliflozin

Conditions

Conditions	Yield
Stage #1: (3R,4S,5S,6R)-2-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol With triethylsilane; boron trifluoride diethyl etherate In dichloromethane at -25 - -10℃; for 2h; Stage #2: With sodium hydrogencarbonate In dichloromethane; water at -10℃; Temperature;	81.36%
With triethylsilane; boron trifluoride diethyl etherate In dichloromethane Inert atmosphere; Cooling with acetone-dry ice; Cooling with ice; enantioselective reaction;	56.7%
With triethylsilane; boron trifluoride diethyl etherate In dichloromethane at 0 - 5℃;

: (2S,3R,4R,5S,6R)-2-[3-[[5-(4-fluorophenyl)-2-thienyl]methyl]-4-methylphenyl]-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol piperdine-4-carboxylic acid complex

: 842133-18-0
canagliflozin

Conditions

Conditions	Yield
In tert-butyl methyl ether; water for 1h;	80%

: 1432591-84-8
2,4-di-O-tert-butyldiphenylsilyl-1-C-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)-β-D-glucopyranoside

: 842133-18-0
canagliflozin

Conditions

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 4h;	73%
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 4h; Inert atmosphere;	68%

: bis(3-[[5-(4-fluorophenyl)-2-thienyl]methyl]-4-methylphenyl)chloroalane

: 498-07-7
levoglucosan

: 842133-18-0
canagliflozin

Conditions

Conditions	Yield
Stage #1: levoglucosan With diisobutylaluminium hydride In toluene at 20℃; for 0.116667h; Inert atmosphere; Schlenk technique; Stage #2: bis(3-[[5-(4-fluorophenyl)-2-thienyl]methyl]-4-methylphenyl)chloroalane In dibutyl ether; toluene at 140℃; for 20h;	50%

: 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

: 842133-18-0
canagliflozin

Conditions

Conditions	Yield
With triethylsilane; boron trifluoride diethyl etherate In 1,1-dichloroethane at -30 - 20℃; for 1.5 - 2h; Product distribution / selectivity;

: 898566-17-1
(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)

: 842133-18-0
canagliflozin

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: trimethylsilylmethyllithium / toluene; diethyl ether; pentane / 0.75 h / -50 °C / Inert atmosphere 1.2: 1 h / 25 °C 2.1: ethyl acetate; toluene / 21 h / 75 °C / Inert atmosphere 3.1: methanol / 16 h / 20 - 60 °C 4.1: water / 1 h / 0 °C View Scheme
Multi-step reaction with 4 steps 1.1: n-hexyllithium / toluene; hexane; cyclopentyl methyl ether / 1.17 h / -45 - -25 °C / Inert atmosphere 2.1: zinc dibromide; lithium bromide / cyclopropyl methyl ether / -25 - 0 °C 2.2: 48.5 h / 20 - 65 °C 3.1: methanol / 16 h / 20 - 60 °C 4.1: water / 1 h / 0 °C View Scheme
Multi-step reaction with 3 steps 1.1: acetic acid; potassium bromide; sodium hydrogencarbonate / water; dichloromethane / 0.25 h / 20 °C 1.2: 20 - 35 °C 1.3: -70 - -30 °C / Inert atmosphere 2.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 0.5 h / -40 - -20 °C / Inert atmosphere 3.1: trimethylsilyl iodide / dichloromethane / 0 - 30 °C View Scheme

: C18H14FLiS

: 842133-18-0
canagliflozin

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: zinc dibromide; lithium bromide / cyclopropyl methyl ether / -25 - 0 °C 1.2: 48.5 h / 20 - 65 °C 2.1: methanol / 16 h / 20 - 60 °C 3.1: water / 1 h / 0 °C View Scheme

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

: 842133-18-0
canagliflozin

Conditions

Conditions	Yield
With water at 0℃; for 1h;

: 1283129-24-7
C36H28F2S2Zn

: 842133-18-0
canagliflozin

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: ethyl acetate; toluene / 21 h / 75 °C / Inert atmosphere 2: methanol / 16 h / 20 - 60 °C 3: water / 1 h / 0 °C View Scheme

: 492-62-6
alpha-D-glucopyranose

: 842133-18-0
canagliflozin

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: triethylamine / dmap / dichloromethane / 20.5 h / 0 - 20 °C / Inert atmosphere 2.1: trimethylsilyl bromide / zinc dibromide / dichloromethane / 24 h / 20 °C / Inert atmosphere 2.2: 0 °C / pH 7 - 8 3.1: n-butyllithium; zinc dibromide / n-heptane; toluene; dibutyl ether / 2.5 h / -10 - 25 °C / Inert atmosphere 3.2: 6.5 h / 95 °C 4.1: methanol / sodium methylate / 16 h / 60 °C View Scheme
Multi-step reaction with 4 steps 1: pyridine; dmap; thionyl chloride / dichloromethane / 2 h / 48 - 50 °C / Reflux; Large scale 2: zinc dibromide; trimethylsilyl bromide / dichloromethane / 10 - 25 °C / Inert atmosphere 3: zinc dibromide; lithium bromide / diethyl ether / -76 °C 4: methanol View Scheme
Multi-step reaction with 4 steps 1.1: pyridine; dmap / dichloromethane / 20.5 h / 0 - 20 °C / Inert atmosphere 2.1: zinc dibromide / dichloromethane / 0.08 h / 20 °C / Inert atmosphere 2.2: 24 h / 20 °C 3.1: isopropylmagnesium chloride; lithium chloride; n-butyllithium / tetrahydrofuran; hexane / 3 h / -10 °C / Inert atmosphere 4.1: water; potassium hydroxide / tetrahydrofuran; methanol / 16 h / 0 - 5 °C View Scheme

: 898566-17-1
(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)

: 81058-27-7
2,3,4,6-tetra-O-pivaloyl-α-D-glucopyranosyl bromide

: 842133-18-0
canagliflozin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: n-butyllithium; zinc dibromide / n-heptane; toluene; dibutyl ether / 2.5 h / -10 - 25 °C / Inert atmosphere 1.2: 6.5 h / 95 °C 2.1: methanol / sodium methylate / 16 h / 60 °C View Scheme

: 1213234-53-7
1,2,3,4,6-penta-O-pivaloyl-D-glucopyranoside

: 842133-18-0
canagliflozin

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: trimethylsilyl bromide / zinc dibromide / dichloromethane / 24 h / 20 °C / Inert atmosphere 1.2: 0 °C / pH 7 - 8 2.1: n-butyllithium; zinc dibromide / n-heptane; toluene; dibutyl ether / 2.5 h / -10 - 25 °C / Inert atmosphere 2.2: 6.5 h / 95 °C 3.1: methanol / sodium methylate / 16 h / 60 °C View Scheme
Multi-step reaction with 3 steps 1: zinc dibromide; trimethylsilyl bromide / dichloromethane / 10 - 25 °C / Inert atmosphere 2: zinc dibromide; lithium bromide / diethyl ether / -76 °C 3: methanol View Scheme

: 1432591-75-7
1,6-anhydro-2,4-di-O-tert-butyldiphenylsilyl-β-D-glucopyranose

: 842133-18-0
canagliflozin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: magnesium / tetrahydrofuran; ethylene dibromide / 2 h / Reflux 1.2: 1 h / 20 °C 1.3: 5 h / 20 - 150 °C 2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: magnesium; ethylene dibromide / tetrahydrofuran / Inert atmosphere; Schlenk technique; Reflux 1.2: 1 h / 20 °C / Inert atmosphere; Schlenk technique; Reflux 2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere View Scheme

: 498-07-7
levoglucosan

: 842133-18-0
canagliflozin

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 1H-imidazole / tetrahydrofuran / 0 °C 2.1: magnesium / tetrahydrofuran; ethylene dibromide / 2 h / Reflux 2.2: 1 h / 20 °C 2.3: 5 h / 20 - 150 °C 3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1.1: 1H-imidazole / tetrahydrofuran / 0 - 20 °C / Inert atmosphere; Schlenk technique 2.1: magnesium; ethylene dibromide / tetrahydrofuran / Inert atmosphere; Schlenk technique; Reflux 2.2: 1 h / 20 °C / Inert atmosphere; Schlenk technique; Reflux 3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere View Scheme

: 32741-93-8
1,6-anhydro-β-D-glucopyranose 2,4-O-phenylboronate

: 842133-18-0
canagliflozin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: water / dimethylsulfoxide-d6 / 1 h / 20 °C / Inert atmosphere 2.1: diisobutylaluminium hydride / toluene / 0.12 h / 20 °C / Inert atmosphere; Schlenk technique 2.2: 20 h / 140 °C View Scheme

: 1030825-20-7
2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene

: 842133-18-0
canagliflozin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: n-butyllithium / toluene; di-isopropyl ether; hexane / 0 °C / Inert atmosphere; Schlenk technique 1.2: 90 °C / Inert atmosphere; Schlenk technique 2.1: diisobutylaluminium hydride / toluene / 0.12 h / 20 °C / Inert atmosphere; Schlenk technique 2.2: 20 h / 140 °C View Scheme
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; toluene; hexane / -75 - -65 °C / Inert atmosphere 1.2: -75 - -70 °C 1.3: 12 h / -75 - 30 °C 2.1: boron trifluoride diethyl etherate; triethylsilane / dichloromethane / 0 - 5 °C View Scheme
Multi-step reaction with 3 steps 1.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere 1.2: 3 h / 20 °C 2.1: triethylsilane; boron trifluoride diethyl etherate / chloroform / 3 h / -40 - 20 °C / Inert atmosphere 3.1: palladium 10% on activated carbon / dichloromethane / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1: n-butyllithium / toluene / -18 - -5 °C 2: methanol / 0 - 20 °C 3: acetonitrile boron trifluoride complex; triethylsilane / n-heptane / 5 h / -5 - 5 °C View Scheme
Multi-step reaction with 5 steps 1.1: sodium iodide; copper(l) iodide; N,N`-dimethylethylenediamine / toluene; diethylene glycol dimethyl ether / 36 h / Inert atmosphere; Reflux 2.1: tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 2.2: 2 h / 0 - 5 °C 2.3: 2 h / Cooling 3.1: 4-methyl-morpholine; dmap / toluene; ethyl acetate / 15 h / 0 - 20 °C 4.1: triethylsilane; boron trifluoride diethyl etherate / acetonitrile / 4 h / 0 °C 5.1: lithium hydroxide monohydrate; water / tetrahydrofuran; methanol / 19.5 h / 20 - 24 °C View Scheme

: 1030825-20-7
2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene

: 74372-90-0
3,4,6-tri-O-benzyl-D-glucal epoxide

: 842133-18-0
canagliflozin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: tri-n-butyllithium magnesate complex / tetrahydrofuran; hexane; diethyl ether / 0.33 h / 0 °C / Inert atmosphere 1.2: 0 - 20 °C / Inert atmosphere 2.1: sodium iodide; chloro-trimethyl-silane / acetonitrile / 1 h / 0 - 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: tri-n-butyllithium magnesate complex / tetrahydrofuran; hexane; diethyl ether / 0.33 h / 0 °C / Inert atmosphere 1.2: 0.5 h / 0 °C / Inert atmosphere 1.3: 0 - 20 °C / Inert atmosphere 2.1: sodium iodide; chloro-trimethyl-silane / acetonitrile / 1 h / 0 - 20 °C View Scheme

: (2S,3S,4R,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)tetrahydro-2H-pyran-3-ol

: 842133-18-0
canagliflozin

Conditions

Conditions	Yield
With chloro-trimethyl-silane; sodium iodide In acetonitrile at 0 - 20℃; for 1h;	0.31 g

: 32469-28-6, 55515-28-1, 55515-29-2, 32384-65-9
(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one

: 842133-18-0
canagliflozin

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: n-butyllithium / tetrahydrofuran; toluene; hexane / 2 h / -70 - -60 °C / Inert atmosphere 2.1: methanesulfonic acid / tetrahydrofuran; toluene; hexane / -70 - 30 °C / Inert atmosphere 3.1: triethylsilane / dichloromethane / -75 - -70 °C 3.2: -75 - 0 °C View Scheme
Multi-step reaction with 3 steps 1.1: n-butyllithium / tetrahydrofuran; toluene; hexane / 1.5 h / -80 - -70 °C 1.2: -80 - -70 °C 1.3: -80 - 20 °C 2.1: n-butyllithium / tetrahydrofuran; toluene; hexane / 1.5 h / -80 - -70 °C 2.2: -80 - -70 °C 2.3: -80 - 20 °C 3.1: triethylsilane / dichloromethane; acetonitrile / 1 h / -55 - -40 °C / Inert atmosphere 3.2: 2 h / -55 - -40 °C View Scheme
Multi-step reaction with 3 steps 1: n-butyllithium / toluene / -18 - -5 °C 2: methanol / 0 - 20 °C 3: acetonitrile boron trifluoride complex; triethylsilane / n-heptane / 5 h / -5 - 5 °C View Scheme
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -75 - -70 °C / Inert atmosphere; Large scale 1.2: 1 h / -60 - 20 °C / Large scale 1.3: Large scale 2.1: lithium hydroxide monohydrate / tetrahydrofuran; methanol / 2 h / 0 - 20 °C View Scheme
Multi-step reaction with 4 steps 1.1: TurboGrignard / tetrahydrofuran / 1 h / -18 - -13 °C / Inert atmosphere; Large scale 1.2: 1 h / -15 - -10 °C / Large scale 1.3: 1 h / 20 °C / Large scale 2.1: dmap; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0 - 10 °C / Large scale 3.1: triethylsilane; boron trifluoride diethyl etherate / acetonitrile; water / 5 - 20 °C / Large scale 4.1: lithium hydroxide; water / tetrahydrofuran; methanol / 2 h / 20 °C / Large scale View Scheme

: 90-80-2
D-Glucono-1,5-lactone

: 842133-18-0
canagliflozin

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: 4-methyl-morpholine / tetrahydrofuran / -10 - 30 °C 2.1: n-butyllithium / tetrahydrofuran; toluene; hexane / 2 h / -70 - -60 °C / Inert atmosphere 3.1: methanesulfonic acid / tetrahydrofuran; toluene; hexane / -70 - 30 °C / Inert atmosphere 4.1: triethylsilane / dichloromethane / -75 - -70 °C 4.2: -75 - 0 °C View Scheme
Multi-step reaction with 4 steps 1.1: trifluoroacetic acid 2.1: s-butylmagnesium chloride; lithium chloride / toluene; tetrahydrofuran / 2 h / -5 - 0 °C 2.2: -45 - -35 °C 3.1: boron trifluoride diethyl etherate; triethylsilane / acetonitrile / 1 h / 30 - 42 °C 4.1: sodium methylate / methanol / 1 h / Reflux View Scheme
Multi-step reaction with 4 steps 1.1: trifluoroacetic acid 2.1: s-butylmagnesium chloride; lithium chloride / toluene; tetrahydrofuran / 2 h / -5 - 0 °C 2.2: -45 - -35 °C 3.1: boron trifluoride diethyl etherate; triethylsilane / acetonitrile / 1 h / 30 - 42 °C 4.1: sodium methylate / methanol / 1 h / Reflux View Scheme
Multi-step reaction with 3 steps 1.1: 4-methyl-morpholine / tetrahydrofuran / 20 °C / Inert atmosphere; Large scale 2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -75 - -70 °C / Inert atmosphere; Large scale 2.2: 1 h / -60 - 20 °C / Large scale 2.3: Large scale 3.1: lithium hydroxide monohydrate / tetrahydrofuran; methanol / 2 h / 0 - 20 °C View Scheme

: 842133-18-0
canagliflozin

: 147-85-3
L-proline

: 1409936-68-0
L-proline-(2S,3R,4R,5S,6R)-2-{3-[5-(4-fluoro-phenyl)-thiophen-2-ylmethyl]-4-methyl-phenyl}-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

Conditions

Conditions	Yield
In n-heptane; ethyl acetate at 60 - 65℃; for 5h; Solvent; Inert atmosphere;	93%
In acetone for 0.166667h; Product distribution / selectivity;
In ethanol; water	0.3 g

: 842133-18-0
canagliflozin

: 108-24-7
acetic anhydride

: 866607-35-4
(3R,4R,5S)-2-(acetoxymethyl)-6-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Conditions

Conditions	Yield
With dmap; triethylamine In ethyl acetate at 20 - 30℃; for 1h;	80%
With 4-methyl-morpholine; dmap In tetrahydrofuran at -10 - 20℃; for 1.25h;	78%
With 4-methyl-morpholine; dmap In dichloromethane at -5 - 5℃; for 4h; Reagent/catalyst;	69.5%

: 498-94-2
isonipecotic acid

: 842133-18-0
canagliflozin

: (2S,3R,4R,5S,6R)-2-[3-[[5-(4-fluorophenyl)-2-thienyl]methyl]-4-methylphenyl]-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol piperdine-4-carboxylic acid complex

Conditions

Conditions	Yield
In water; acetone at 40℃; for 6h; Solvent;	80%

: 842133-18-0
canagliflozin

: 42856-71-3
(S)-2-methylpyrrolidine-2-carboxylic acid

: (2S,3R,4R,5S,6R)-2-[3-[[5-(4-fluorophenyl)thiophen-2-yl]methyl]-4-methylphenyl]-6-(hydroxymethyl)oxane-3,4,5-triol alpha-methyl-L-proline

Conditions

Conditions	Yield
In dichloromethane at 20 - 30℃; Reagent/catalyst;	66%

: 842133-18-0
canagliflozin

: (2S,3R,4R,5S,6R)-2-(3-((5-(4-fluorophenyl)thiophen-2-yl)(hydroperoxy)methyl)-4-methylphenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Conditions

Conditions	Yield
Stage #1: canagliflozin With dihydrogen peroxide In water; acetonitrile at 60℃; for 12h; Stage #2: With dihydrogen peroxide; fluorophosphoric acid In water; acetonitrile at 25℃; for 48h;	35%
Multi-step reaction with 3 steps 1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / ethanol / 24 h / 20 °C 2: sodium tetrahydroborate / tetrahydrofuran / 5 h / 20 °C / Inert atmosphere 3: dihydrogen peroxide; sulfuric acid / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere View Scheme

: 842133-18-0
canagliflozin

: 108-24-7
acetic anhydride

A: C31H33FO7S

B: C28H29FO7S

Conditions

Conditions	Yield
With 4-methyl-morpholine In dichloromethane at -10 - 20℃; for 1h;	A 19.1% B 21.4%

...Expand

: 842133-18-0
canagliflozin

: (1S)-1,5-anhydro-1-[3-[[5-(4-fluorophenyl)-2-thienyl]methyl]-4-methylphenyl]-D-glucitol hemihydrate

Conditions

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

Canagliflozin Specification

The Canagliflozin, with the CAS registry number 842133-18-0, is also known as D-Glucitol, 1,5-anhydro-1-C-(3-((5-(4-fluorophenyl)-2-thienyl)methyl)-4- methylphenyl)-, (1S)-. This chemical's molecular formula is C₂₄H₂₅FO₅S and molecular weight is 444.52. What's more, its systematic name is called (1S)-1,5-Anhydro-1-(3-{[5-(4-fluorophenyl)-2-thienyl]methyl}-4-methylphenyl)-D-glucitol. Canagliflozin is an experimental drug. It is an inhibitor of subtype 2 sodium-glucose transport protein (SGLT2), which is responsible for at least 90 % of the glucose reabsorption in the kidney.

Physical properties about Canagliflozin are: (1)ACD/LogP: 5.34±0.81; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 5.34; (4)ACD/LogD (pH 7.4): 5.34; (5)ACD/BCF (pH 5.5): 6705.27; (6)ACD/BCF (pH 7.4): 6705.24; (7)ACD/KOC (pH 5.5): 19078.31; (8)ACD/KOC (pH 7.4): 19078.25; (9)#H bond acceptors: 5; (10)#H bond donors: 4; (11)#Freely Rotating Bonds: 9; (12)Polar Surface Area: 118.39 Å²; (13)Index of Refraction: 1.639; (14)Molar Refractivity: 117.2±0.3 cm³; (15)Molar Volume: 325.9±3.0 cm³; (16)Polarizability: 46.5±0.5×10^-24cm³; (17)Surface Tension: 56.1±3.0 dyne/cm; (18)Density: 1.4±0.1 g/cm³; (19)Flash Point: 342.6±31.5 °C; (20)Enthalpy of Vaporization: 99.7±3.0 kJ/mol; (21)Boiling Point: 642.9±55.0 °C at 760 mmHg; (22)Vapour Pressure: 0.0±2.0 mmHg at 25 °C.

You can still convert the following datas into molecular structure:
(1) SMILES: Cc1ccc(cc1Cc2ccc(s2)c3ccc(cc3)F)[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O
(2) InChI: InChI=1S/C24H25FO5S/c1-13-2-3-15(24-23(29)22(28)21(27)19(12-26)30-24)10-16(13)11-18-8-9-20(31-18)14-4-6-17(25)7-5-14/h2-10,19,21-24,26-29H,11-12H2,1H3/t19-,21-,22+,23-,24+/m1/s1
(3) InChIKey: XTNGUQKDFGDXSJ-ZXGKGEBGSA-N

Product Name

Canagliflozin

Synthetic route

Canagliflozin Specification

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