1-(β-D-glucopyranosyl)-4-methyl-3-[(5-(3-pyridyl)-2-thienyl)methyl]benzene

Base Information

• Chemical Name: 1-(β-D-glucopyranosyl)-4-methyl-3-[(5-(3-pyridyl)-2-thienyl)methyl]benzene
• CAS No.: 842134-14-9
• Molecular Formula: C₂₃H₂₅NO₅S
• Molecular Weight: 427.521
• Mol file: 842134-14-9.mol

Synonyms:1-(β-D-glucopyranosyl)-4-methyl-3-[(5-(3-pyridyl)-2-thienyl)methyl]benzene

Chemical Property of 1-(β-D-glucopyranosyl)-4-methyl-3-[(5-(3-pyridyl)-2-thienyl)methyl]benzene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(β-D-glucopyranosyl)-4-methyl-3-[(5-(3-pyridyl)-2-thienyl)methyl]benzene

There total 6 articles about 1-(β-D-glucopyranosyl)-4-methyl-3-[(5-(3-pyridyl)-2-thienyl)methyl]benzene 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: 30.0%

1-(1-methoxy-D-glucopyranosyl)-4-methyl-3-[(5-(3-pyridyl)-2-thienyl)methyl]benzene (1450738-09-6) → 1-(β-D-glucopyranosyl)-4-methyl-3-[(5-(3-pyridyl)-2-thienyl)methyl]benzene (842134-14-9)

Guidance literature:

With triethylsilane; boron trifluoride diethyl etherate; In chloroform; at -78 - 0 ℃; for 3h; diastereoselective reaction;

DOI:10.1016/j.bmc.2013.05.048

Reference yield:

5-bromo-2-methylbenzaldehyde (90050-59-2) → 1-(β-D-glucopyranosyl)-4-methyl-3-[(5-(3-pyridyl)-2-thienyl)methyl]benzene (842134-14-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: n-butyllithium / hexane; tetrahydrofuran / -78 - 0 °C / Inert atmosphere

1.2: 1 h / -78 °C / Inert atmosphere

2.1: trifluoroacetic acid; sodium tris(acetoxy)borohydride / 1.58 h / 0 - 20 °C / Inert atmosphere

3.1: n-butyllithium / toluene; hexane; tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

3.2: 3 h / -78 °C / Inert atmosphere

4.1: methanesulfonic acid / toluene; hexane; tetrahydrofuran / -78 - 20 °C / Inert atmosphere

5.1: triethylsilane; boron trifluoride diethyl etherate / chloroform / 3 h / -78 - 0 °C

With triethylsilane; n-butyllithium; methanesulfonic acid; boron trifluoride diethyl etherate; sodium tris(acetoxy)borohydride; trifluoroacetic acid; In tetrahydrofuran; hexane; chloroform; toluene; 3.2: |Barbier Coupling Reaction;

DOI:10.1016/j.bmc.2013.05.048

Reference yield:

(5-bromo-2-methylphenyl)(5-(pyridin-3-yl)thiophen-2-yl)methanol (1450738-08-5) → 1-(β-D-glucopyranosyl)-4-methyl-3-[(5-(3-pyridyl)-2-thienyl)methyl]benzene (842134-14-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: trifluoroacetic acid; sodium tris(acetoxy)borohydride / 1.58 h / 0 - 20 °C / Inert atmosphere

2.1: n-butyllithium / toluene; hexane; tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

2.2: 3 h / -78 °C / Inert atmosphere

3.1: methanesulfonic acid / toluene; hexane; tetrahydrofuran / -78 - 20 °C / Inert atmosphere

4.1: triethylsilane; boron trifluoride diethyl etherate / chloroform / 3 h / -78 - 0 °C

With triethylsilane; n-butyllithium; methanesulfonic acid; boron trifluoride diethyl etherate; sodium tris(acetoxy)borohydride; trifluoroacetic acid; In tetrahydrofuran; hexane; chloroform; toluene; 2.2: |Barbier Coupling Reaction;

DOI:10.1016/j.bmc.2013.05.048

upstream raw materials:

(5-bromo-2-methylphenyl)(5-(pyridin-3-yl)thiophen-2-yl)methanol

3-thiophen-2-yl-pyridine

5-bromo-2-methylbenzaldehyde

3-[5-(5-bromo-2-methylbenzyl)thiophen-2-yl]pyridine