1-{4-chloro-3-[(dimethyl)(4-ethyloxyphenyl)methyl]phenyl}-1-deoxy-α/β-D-glucopyranose

Base Information

• Chemical Name: 1-{4-chloro-3-[(dimethyl)(4-ethyloxyphenyl)methyl]phenyl}-1-deoxy-α/β-D-glucopyranose
• CAS No.: 1318794-42-1
• Molecular Formula: C₂₃H₂₉ClO₆
• Molecular Weight: 436.933
• Mol file: 1318794-42-1.mol

Synonyms:1-{4-chloro-3-[(dimethyl)(4-ethyloxyphenyl)methyl]phenyl}-1-deoxy-α/β-D-glucopyranose

Chemical Property of 1-{4-chloro-3-[(dimethyl)(4-ethyloxyphenyl)methyl]phenyl}-1-deoxy-α/β-D-glucopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-{4-chloro-3-[(dimethyl)(4-ethyloxyphenyl)methyl]phenyl}-1-deoxy-α/β-D-glucopyranose

There total 10 articles about 1-{4-chloro-3-[(dimethyl)(4-ethyloxyphenyl)methyl]phenyl}-1-deoxy-α/β-D-glucopyranose 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-{4-chloro-3-[(dimethyl)(4-ethyloxyphenyl)methyl]phenyl}-α/β-D-methyl glucopyranoside (1318794-41-0) → 1-{4-chloro-3-[(dimethyl)(4-ethyloxyphenyl)methyl]phenyl}-1-deoxy-α/β-D-glucopyranose (1318794-42-1)

Guidance literature:

With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; at 20 ℃; Cooling with ice;

Reference yield:

C24H31ClO6 → 1-{4-chloro-3-[(dimethyl)(4-ethyloxyphenyl)methyl]phenyl}-1-deoxy-α/β-D-glucopyranose (1318794-42-1)

Guidance literature:

With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; at 0 - 20 ℃;

DOI:10.1002/cjoc.201190222

Reference yield:

5-Bromo-2-chloro-benzoic acid ethyl ester (76008-73-6) → 1-{4-chloro-3-[(dimethyl)(4-ethyloxyphenyl)methyl]phenyl}-1-deoxy-α/β-D-glucopyranose (1318794-42-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: tetrahydrofuran / 0.5 h / 0 - 5 °C / Inert atmosphere

2.1: aluminum (III) chloride / dichloromethane / 3.25 h / 0 - 20 °C

3.1: n-butyllithium / tetrahydrofuran; ethanol; hexane; nitrogen / 0.5 h / -78 °C / Inert atmosphere; liquid N₂

3.2: 0.5 h / -78 °C / Inert atmosphere; liquid N₂

3.3: 20 °C / Inert atmosphere; liquid N₂

4.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 0 - 20 °C

With triethylsilane; aluminum (III) chloride; n-butyllithium; boron trifluoride diethyl etherate; In tetrahydrofuran; ethanol; hexane; dichloromethane; nitrogen; 2.1: Friedel Crafts alkylation;

DOI:10.1002/cjoc.201190222

upstream raw materials:

(5-bromo-2-chlorophenyl)(4-ethyloxyphenyl)(dimethyl)methane

1-(5-bromo-2-chlorophenyl)-1-methylethanol

5-bromo-2-chlorobenzoic acid

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

Downstream raw materials:

1-{4-chloro-3-[(dimethyl)(4-ethyloxyphenyl)methyl]phenyl}-1-deoxy-β-D-glucopyranose

2,3,4,6-tetra-O-acetyl-1-deoxy-1-{4-chloro-3-[1-(4-ethoxyphenyl)-1-methylethyl]phenyl}-β-D-glucopyranose