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Basic Information

Molecular Structure:
CAS No.:	842133-18-0
Name:	Canagliflozin
Article Data:	45

Formula:	C₂₄H₂₅FO₅S
Molecular Weight:	444.524
Synonyms:	(1S)-1,5-Anhydro-1-(3-{[5-(4-fluorophenyl)-2-thienyl]methyl}-4-methylphenyl)-D-glucitol;
EINECS:	695-192-1
Density:	1.4±0.1 g/cm³
Boiling Point:	642.9±55.0 °C at 760 mmHg
Flash Point:	342.6±31.5 °C
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℃;

Raw Materials

498-07-7

81058-27-7

492-62-6

898566-17-1

1030825-21-8

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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