Dapagliflozin Impurity 10

Base Information

• Chemical Name: Dapagliflozin Impurity 10
• CAS No.: 960404-86-8
• Molecular Formula: C₂₁H₂₅ClO₇
• Molecular Weight: 424.878
• Mol file: 960404-86-8.mol

Synonyms:(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetraol

Chemical Property of Dapagliflozin Impurity 10

Chemical Property:

• Boiling Point: 618.3±55.0 °C(Predicted)
• PKA: 11.10±0.70(Predicted)
• Density: 1.423±0.06 g/cm3(Predicted)

Purity/Quality:

97% ^*data from raw suppliers

DapagliflozinHydroxyImpurity ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: Dapagliflozin Hydroxy Impurity, is an impurity of Dapagliflozin (D185370), a sodium-glucose transporter 2 inhibitor.

Technology Process of Dapagliflozin Impurity 10

There total 3 articles about Dapagliflozin Impurity 10 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:

1-chloro-2-(4-ethoxybenzyl)-4-iodobenzene (1103738-29-9) + (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-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetraol (960404-86-8)

Guidance literature:

1-chloro-2-(4-ethoxybenzyl)-4-iodobenzene; With TurboGrignard; In tetrahydrofuran; at -60 - -50 ℃; for 0.666667h; Inert atmosphere;

(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one; In tetrahydrofuran; n-heptane; at -60 - -50 ℃; for 5.5h;

With water; ammonium chloride; at -15 - 15 ℃; for 12.5h;

Reference yield:

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene (461432-23-5) + (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-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetraol (960404-86-8)

Guidance literature:

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene; With n-butyllithium; In tetrahydrofuran; at -78 ℃; Inert atmosphere;

(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one; In tetrahydrofuran; at -78 ℃; for 2.5h; Inert atmosphere;

With water; trifluoroacetic acid; In tetrahydrofuran;

Reference yield:

1-chloro-2-(4-ethoxybenzyl)-4-iodobenzene (1103738-29-9) + (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-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetraol (960404-86-8) + C21H27ClO7

Guidance literature:

1-chloro-2-(4-ethoxybenzyl)-4-iodobenzene; With TurboGrignard; In tetrahydrofuran; at -20 - -10 ℃; for 0.666667h; Inert atmosphere;

(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one; In tetrahydrofuran; n-heptane; at -20 - -10 ℃; for 5.5h;

With water; ammonium chloride; at -15 - 15 ℃; for 12.5h;

upstream raw materials:

1-chloro-2-(4-ethoxybenzyl)-4-iodobenzene

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

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene

Downstream raw materials:

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