Name: Empagliflozin
SKU: 864070-44-0

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Pharmaceutical (415)
Organic Chemicals (32)
Others (18)
Reagent (6)
Materials (5)
Catalyst and Auxiliary (2)
(1)
Synthetic Flavours & Fragrances (1)
Basic Inorganic Chemicals (1)

Basic Information

Molecular Structure:
CAS No.:	864070-44-0
Name:	Empagliflozin
Article Data:	44

Formula:	C₂₃H₂₇ClO₇
Molecular Weight:	450.916
Synonyms:	(2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-((S)-tetrahydrofuran-3-yloxy)benzyl)phenyl)-6-(hydroxyMethyl)-tetrahydro-2H-pyran-3,4,5-triol;Empaglifloin;Glyxambi;mpagliflozin;(1S)-1,5-Anhydro-1-C-[4-chloro-3-[[4-[[(3S)-tetrahydro-3-furanyl]oxy]phenyl]methyl]phenyl]-D-glucitol;ozin;Empag;CS-798;EmpagL;BI-10773
EINECS:	620-176-8
Density:	1.398
Boiling Point:	665℃
Flash Point:	356℃
PSA:	108.61000
LogP:	1.61340

Synthetic route

: C29H32BrClO9

: 864070-44-0
empagliflozin

Conditions

Conditions	Yield
With water; potassium hydroxide In acetonitrile at 50 - 60℃; Reagent/catalyst;	93.8%

: (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)tetrahydro-2H-pyran-3,4,5-trityl triacetate

: 864070-44-0
empagliflozin

Conditions

Conditions	Yield
With potassium carbonate In tetrahydrofuran at 40 - 45℃;	93%
With sodium hydroxide In methanol at 20℃; for 1h;	91.7%
With lithium hydroxide In methanol; water at 0 - 5℃; Reagent/catalyst;	89.2%

: C51H43ClO11

: 864070-44-0
empagliflozin

Conditions

Conditions	Yield
With sodium methylate In tetrahydrofuran at 40 - 45℃;	90%

: C43H59ClO11

: 864070-44-0
empagliflozin

Conditions

Conditions	Yield
With lithium hydroxide In ethanol; water at 40 - 45℃;	87%

: 1279691-36-9
(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

: 864070-44-0
empagliflozin

Conditions

Conditions	Yield
With triethylsilane; aluminum (III) chloride In dichloromethane; acetonitrile	82.5%
With triethylsilane; aluminum (III) chloride In dichloromethane; acetonitrile at -5 - 10℃; for 2h; Large scale;	78%
Stage #1: (2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol With aluminum (III) chloride In dichloromethane; acetonitrile at 5℃; for 0.5h; Large scale; Stage #2: With triethylsilane In dichloromethane; acetonitrile at 10℃; for 2h; Large scale;	78%

: C40H63ClO7Si2

: 864070-44-0
empagliflozin

Conditions

Conditions	Yield
Stage #1: C40H63ClO7Si2 With tetrabutyl ammonium fluoride In tetrahydrofuran at 60℃; for 6h; Large scale; Stage #2: With ethanol In toluene at 0 - 75℃; for 2.5h; Large scale;	81%

: 2,3,4,6-tetra-O-benzyl-1-deoxy-1-((S)-(4-chloro-3-(4-(tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-β-D-glucopyranose

: 864070-44-0
empagliflozin

Conditions

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 18h; Reagent/catalyst;	80%

: 915095-94-2
(3S)-3-[4-[(2-chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran

: 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

: 864070-44-0
empagliflozin

Conditions

Yield

Stage #1: (3S)-3-[4-[(2-chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran With isopropylmagnesium chloride; lithium chloride In tetrahydrofuran at -21 - -15℃; for 1.83333h;
Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one In dichloromethane; acetonitrile at -25 - -13℃; for 2.91667h;

73%

Stage #1: (3S)-3-[4-[(2-chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran With isopropylmagnesium chloride; lithium chloride In tetrahydrofuran at -21 - -15℃; for 1.83333h; Industry scale;
Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran at -25 - -18℃; for 2.91667h; Industry scale;
Stage #3: With citric acid In water at -13 - 19℃; Product distribution / selectivity; Industry scale;

73%