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Dapagliflozin
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Name

Dapagliflozin

 EINECS 639-683-0
CAS No. 461432-26-8 Density 1.349 g/cm3
PSA 99.38000 LogP 1.84440
Solubility N/A Melting Point N/A
Formula C21H25ClO6 Boiling Point 609.045 °C at 760 mmHg
Molecular Weight 408.879 Flash Point 322.139 °C
Transport Information N/A Appearance N/A
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 461432-26-8 (Dapagliflozin) Hazard Symbols N/A
Synonyms

BMS 512148;(1S)-1,5-Anhydro-1-C-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-D-glucitol;D-Glucitol,1,5-anhydro-1-C-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-, (1S)-;

Article Data 51

Dapagliflozin Synthetic route

461432-25-7

(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-ethoxybenzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

461432-26-8

dapagliflozin

Conditions
ConditionsYield
With lithium hydroxide In tetrahydrofuran; ethanol100%
With water; sodium carbonate In methanol at 25 - 50℃; for 6h; Time; Reagent/catalyst;96.18%
With lithium hydroxide In tetrahydrofuran; methanol; water at 0 - 20℃;95%

C21H25ClO6*C3H8O2

461432-26-8

dapagliflozin

Conditions
ConditionsYield
In n-heptane; tert-butyl methyl ether at -15 - 50℃; Inert atmosphere;98.7%

(3R,4S,5S,6R)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-2-ethoxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

461432-26-8

dapagliflozin

Conditions
ConditionsYield
With triethylsilane; boron trifluoride diethyl etherate In methanol; dichloromethane; acetonitrile at -20 - 20℃; for 5h;97.3%
With triethylsilane; boron trifluoride diethyl etherate In dichloromethane; acetonitrile at -20 - 0℃; for 5h; Molecular sieve; Inert atmosphere; Large scale; diastereoselective reaction;79%

(2R,3R,4R,5S,6S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-(4-chloro-3-(4-ethoxybenzyl)phenyl)tetrahydro-2H-pyran

461432-26-8

dapagliflozin

Conditions
ConditionsYield
With 5%-palladium/activated carbon; hydrogen In ethyl acetate at 20℃; for 24h; Autoclave;97%

(2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol bis(L-proline) cocrystal

461432-26-8

dapagliflozin

Conditions
ConditionsYield
In water; ethyl acetate at 80℃;95%
With water In methanol at 20 - 25℃; for 16h;94%
With water In methanol at 20 - 25℃; for 17h; Reflux;94%

(2-chloro-5-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-2-yl)phenyl)(4-ethoxyphenyl)methanone

461432-26-8

dapagliflozin

Conditions
ConditionsYield
With triethylsilane; boron trifluoride diethyl etherate In dichloromethane; acetonitrile at -25 - 35℃; for 7h; Inert atmosphere;95%

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol bis(L-proline) cocrystal

461432-26-8

dapagliflozin

Conditions
ConditionsYield
Stage #1: (2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol bis(L-proline) cocrystal With methanol for 0.333333h; Reflux;
Stage #2: With water at 20 - 25℃; for 16.6667h;		94%

C27H30BrClO8

461432-26-8

dapagliflozin

Conditions
ConditionsYield
With water; potassium hydroxide In acetonitrile at 50 - 60℃; Reagent/catalyst;91.3%
714269-57-5

(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol

461432-26-8

dapagliflozin

Conditions
ConditionsYield
With triethylsilane; boron trifluoride diethyl etherate at 5℃; for 0.00416667h; Temperature;87.6%
With triethylsilane; aluminum (III) chloride In dichloromethane; acetonitrile at -5 - 10℃; for 3.5h; Large scale;76%
Stage #1: (2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol With aluminum (III) chloride In dichloromethane; acetonitrile at -5℃; for 0.5h; Autoclave; Large scale;
Stage #2: With triethylsilane In dichloromethane; acetonitrile at 10℃; for 3h; Large scale;		76%
461432-24-6

(3R,4S,5S,6R)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

461432-26-8

dapagliflozin

Conditions
ConditionsYield
With triethylsilane; boron trifluoride diethyl etherate In methanol; dichloromethane; ethyl acetate at -20 - 20℃; for 5h;83.1%
Stage #1: (3R,4S,5S,6R)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol With triethylsilane; boron trifluoride diethyl etherate In dichloromethane; acetonitrile at -10 - 20℃;
Stage #2: With water; sodium hydrogencarbonate In dichloromethane; acetonitrile		44%
With triethylsilane; boron trifluoride diethyl etherate In dichloromethane; acetonitrile at -10℃; for 1.5h; Temperature; Time; Inert atmosphere;

Dapagliflozin Specification

The Dapagliflozin, with the CAS registry number 461432-26-8, is also known as (1S)-1,5-Anhydro-1-C-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-D-glucitol. It belongs to the product categories of Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals.This chemical's molecular formula is C21H25ClO6 and molecular weight is 408.87.Its EINECS number is 204-115-9. What's more,Its systematic name is D-Glucitol,1,5-anhydro-1-C-(4-chloro-3-((4-ethoxyphenyl)methyl)phenyl)-,(1S)-.It is one kind of white crystalline powder, odorless, little bitter taste.And it is the treatment of type 1 or type 2 diabetes, or any condition causing hyperglycemia.

Physical properties about Dapagliflozin are:
 (1)ACD/LogP: 2.09; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.09; (4)ACD/LogD (pH 7.4): 2.09; (5)ACD/BCF (pH 5.5): 22.83; (6)ACD/BCF (pH 7.4): 22.83; (7)ACD/KOC (pH 5.5): 326.57; (8)ACD/KOC (pH 7.4): 326.57; (9)#H bond acceptors: 6; (10)#H bond donors: 4; (11)#Freely Rotating Bonds: 10; (12)Index of Refraction: 1.614; (13)Molar Refractivity: 105.629 cm3 ; (14)Molar Volume: 303.074 cm3; (15)Surface Tension: 54.3219985961914 dyne/cm; (16)Density: 1.349 g/cm3; (17)Flash Point: 322.139 °C; (18)Enthalpy of Vaporization: 95.131 kJ/mol; (19)Boiling Point: 609.045 °C at 760 mmHg; (20)Vapour Pressure: 0 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES:Clc1ccc(cc1Cc2ccc(OCC)cc2)[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O;
(2)Std. InChI:InChI=1S/C21H25ClO6/c1-2-27-15-6-3-12(4-7-15)9-14-10-13(5-8-16(14)22)21-20(26)19(25)18(24)17(11-23)28-21/h3-8,10,17-21,23-26H,2,9,11H2,1H3/t17-,18-,19+,20-,21+/m1/s1;
(3)Std. InChIKey:JVHXJTBJCFBINQ-ADAARDCZSA-N.

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