(2S,3R,4R,5S,6R)-2-(2,4-dichloro-5-((5-(thiophen-3-yl)thiazol-2-yl)methyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Base Information

• Chemical Name: (2S,3R,4R,5S,6R)-2-(2,4-dichloro-5-((5-(thiophen-3-yl)thiazol-2-yl)methyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
• CAS No.: 1313513-27-7
• Molecular Formula: C₂₀H₁₉Cl₂NO₅S₂
• Molecular Weight: 488.413
• Mol file: 1313513-27-7.mol

Synonyms:(2S,3R,4R,5S,6R)-2-(2,4-dichloro-5-((5-(thiophen-3-yl)thiazol-2-yl)methyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Chemical Property of (2S,3R,4R,5S,6R)-2-(2,4-dichloro-5-((5-(thiophen-3-yl)thiazol-2-yl)methyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4R,5S,6R)-2-(2,4-dichloro-5-((5-(thiophen-3-yl)thiazol-2-yl)methyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

There total 12 articles about (2S,3R,4R,5S,6R)-2-(2,4-dichloro-5-((5-(thiophen-3-yl)thiazol-2-yl)methyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol 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:

C48H43Cl2NO5S2 → (2S,3R,4R,5S,6R)-2-(2,4-dichloro-5-((5-(thiophen-3-yl)thiazol-2-yl)methyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (1313513-27-7)

Guidance literature:

C₄₈H₄₃Cl₂NO₅S₂; With trimethylsilyl iodide; In acetonitrile; at 0 - 50 ℃; Inert atmosphere;

With methanol; In acetonitrile;

DOI:10.1016/j.ejmech.2011.03.052

Reference yield:

C48H45Cl2NO7S → (2S,3R,4R,5S,6R)-2-(2,4-dichloro-5-((5-(thiophen-3-yl)thiazol-2-yl)methyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (1313513-27-7)

Guidance literature:

Multi-step reaction with 2 steps

1: Lawessons reagent / tetrahydrofuran / Inert atmosphere; Reflux

2: trimethylsilyl iodide / acetonitrile / 0 - 50 °C / Inert atmosphere

With Lawessons reagent; trimethylsilyl iodide; In tetrahydrofuran; acetonitrile;

DOI:10.1016/j.ejmech.2011.03.052

Reference yield:

C50H60Cl2O6Si → (2S,3R,4R,5S,6R)-2-(2,4-dichloro-5-((5-(thiophen-3-yl)thiazol-2-yl)methyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (1313513-27-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C / Inert atmosphere

2.1: pyridine; phosphorus tribromide / diethyl ether / 0 - 20 °C / Inert atmosphere; Reflux

2.2: 85 °C / Inert atmosphere

3.1: sodium hydroxide / ethanol; water / 100 °C / Inert atmosphere

3.2: 0 °C

4.1: 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

5.1: Lawessons reagent / tetrahydrofuran / Inert atmosphere; Reflux

6.1: trimethylsilyl iodide / acetonitrile / 0 - 50 °C / Inert atmosphere

With Lawessons reagent; 4-methyl-morpholine; pyridine; trimethylsilyl iodide; tetrabutyl ammonium fluoride; phosphorus tribromide; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium hydroxide; In tetrahydrofuran; diethyl ether; ethanol; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/j.ejmech.2011.03.052

upstream raw materials:

(5-bromo-2,4-dichlorobenzyloxy)triisopropylsilane

2-(2,4-dichloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)phenyl)acetic acid

2,4 dichlorobenzoic acid

5-bromo-2,4-dichloro benzoic acid

Refernces

• 1、 -. "THIAZOLE DERIVATIVES AS SGLT2 INHIBITORS AND PHARMACEUTICAL COMPOSITION COMPRISING SAME". Page/Page column 78. . Retrieved 2012/01/06.