(2-chloro-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)phenyl) (4-(((S)-tetrahydrofuran-3-yl)oxy)phenyl)methanone

Base Information

• Chemical Name: (2-chloro-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)phenyl) (4-(((S)-tetrahydrofuran-3-yl)oxy)phenyl)methanone
• CAS No.: 2125472-55-9
• Molecular Formula: C₂₃H₂₅ClO₈
• Molecular Weight: 464.9
• Mol file: 2125472-55-9.mol

Synonyms:

Chemical Property of (2-chloro-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)phenyl) (4-(((S)-tetrahydrofuran-3-yl)oxy)phenyl)methanone

Chemical Property:

• Boiling Point: 710.3±60.0 °C(Predicted)
• Density: 1.447±0.06 g/cm3(Predicted)

Purity/Quality:

NLT 98% ^*data from raw suppliers

(2-Chloro-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)phenyl)(4-(((S)-tetrahydrofuran-3-yl)oxy)phenyl)methanone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: (2-Chloro-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)phenyl)(4-(((S)-tetrahydrofuran-3-yl)oxy)phenyl)methanone is an impurity of Empagliflozin (E521510), a novel, potent and selective SGLT-2 inhibitor. It improves glycaemic control syndrome in diabetic rats.

Technology Process of (2-chloro-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)phenyl) (4-(((S)-tetrahydrofuran-3-yl)oxy)phenyl)methanone

There total 11 articles about (2-chloro-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)phenyl) (4-(((S)-tetrahydrofuran-3-yl)oxy)phenyl)methanone 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:

[2-chloro-5-[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)-2 methoxy-tetrahydropyran-2-yl]phenyl]-[4-[(3S)-tetrahydrofuran-3-yl]oxyphenyl]methanone → (2-chloro-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)phenyl) (4-(((S)-tetrahydrofuran-3-yl)oxy)phenyl)methanone (2125472-55-9)

Guidance literature:

With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; acetonitrile; at -15 - 5 ℃; for 2h;

Reference yield:

(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) → (2-chloro-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)phenyl) (4-(((S)-tetrahydrofuran-3-yl)oxy)phenyl)methanone (2125472-55-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-butyllithium / 2-methyltetrahydrofuran; hexane / 2 h / -78 °C

1.2: 20 h / 20 - 45 °C

2.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane; acetonitrile / 2 h / -15 - 5 °C

With triethylsilane; n-butyllithium; boron trifluoride diethyl etherate; In 2-methyltetrahydrofuran; hexane; dichloromethane; acetonitrile;

Reference yield:

C31H33ClO12 → (2-chloro-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)phenyl) (4-(((S)-tetrahydrofuran-3-yl)oxy)phenyl)methanone (2125472-55-9)

Guidance literature:

With methanol; sodium hydroxide; at 20 ℃; for 8h;

upstream raw materials:

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

4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-chlorobenzene

4-Fluorobenzoic acid

4-fluorobenzoyl chloride