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

Base Information

• Chemical Name: 4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-chlorobenzene
• CAS No.: 135700-53-7
• Molecular Formula: C₂₀H₂₃ClO₉
• Molecular Weight: 442.85
• Mol file: 135700-53-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 10 articles about 4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-chlorobenzene 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: 58.0%

methyl 1-C-(4-chlorophenyl)-2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside → 4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-chlorobenzene (135700-53-7)

Guidance literature:

With triethylsilane; boron trifluoride diethyl etherate; water; In acetonitrile; at -7.5 - 20 ℃; for 39.3333h;

Reference yield: 50.0%

2,3,4,6-tetra-O-acetyl-1-O-trifluoroacetyl-β-D-glucopyranose (78942-85-5) + chlorobenzene (108-90-7) → 4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-chlorobenzene (135700-53-7)

Guidance literature:

With boron trifluoride diethyl etherate; In acetonitrile; Reflux;

Reference yield:

methyl 1-C-(4-chlorophenyl)-2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside → 4-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-chlorobenzene + 4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-chlorobenzene (135700-53-7)

Guidance literature:

With triethylsilane; boron trifluoride diethyl etherate; water; In acetonitrile; at 0 - 15 ℃; for 0.333333h;

DOI:10.1021/jo071051i

upstream raw materials:

(4-chlorphenyl)magnesium bromide

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl chloride

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

D-Glucono-1,5-lactone

Downstream raw materials:

(1S)-2,3,4,6-tetra-O-acetyl-1,5-anhydro-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-D-glucitol

empagliflozin

(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

(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