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

Base Information

Chemical Name:1-(β-D-glucopyranosyl)-4-methyl-3-[(5-(2-pyrimidyl)-2-thienyl)methyl]benzene
CAS No.:842134-42-3
Molecular Formula:C₂₂H₂₄N₂O₅S
Molecular Weight:428.509
Hs Code.:

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

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

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

There total 11 articles about 1-(β-D-glucopyranosyl)-4-methyl-3-[(5-(2-pyrimidyl)-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: 55.0%

: 866607-37-6
4-methyl-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-3-[(5-(2-pyrimidyl)-2-thienyl)methyl]benzene

: 842134-42-3
1-(β-D-glucopyranosyl)-4-methyl-3-[(5-(2-pyrimidyl)-2-thienyl)methyl]benzene

Guidance literature:: With sodium methylate; In tetrahydrofuran; methanol; at 20 ℃; for 1h;
DOI:10.1016/j.bmc.2013.05.048

Reference yield:

: 21900-41-4
5-bromo-2-methylbenzoyl?chloride

: 842134-42-3
1-(β-D-glucopyranosyl)-4-methyl-3-[(5-(2-pyrimidyl)-2-thienyl)methyl]benzene

Guidance literature:: Multi-step reaction with 10 steps

1.1: aluminum (III) chloride / dichloromethane / 0 - 20 °C

2.1: triethylsilane; boron trifluoride diethyl etherate / chloroform; acetonitrile / 0 - 20 °C

3.1: n-butyllithium / toluene; hexane; tetrahydrofuran / 0.42 h / -78 °C / Inert atmosphere

3.2: 1.33 h / -78 °C / Inert atmosphere

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

5.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 2 h / -78 - 0 °C / Inert atmosphere

6.1: pyridine; dmap / chloroform / 1 h / 20 °C

7.1: palladium 10% on activated carbon; triethylamine; hydrogen / methanol; tetrahydrofuran / 18 h / 20 °C

8.1: pyridine; bromine / chloroform / 0.17 h / 0 - 20 °C

9.1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / 1-methyl-pyrrolidin-2-one / 3.5 h / 100 °C / Inert atmosphere

10.1: sodium methylate / methanol; tetrahydrofuran / 1 h / 20 °C

With pyridine; triethylsilane; dmap; aluminum (III) chloride; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; n-butyllithium; methanesulfonic acid; palladium 10% on activated carbon; boron trifluoride diethyl etherate; hydrogen; bromine; sodium methylate; triethylamine; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; methanol; hexane; dichloromethane; chloroform; toluene; acetonitrile; 3.2: |Barbier Coupling Reaction;
DOI:10.1016/j.bmc.2013.05.048

Reference yield:

: C₃₀H₅₃ClO₆SSi₄

: 842134-42-3
1-(β-D-glucopyranosyl)-4-methyl-3-[(5-(2-pyrimidyl)-2-thienyl)methyl]benzene

Guidance literature:: Multi-step reaction with 7 steps

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

2: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 2 h / -78 - 0 °C / Inert atmosphere

3: pyridine; dmap / chloroform / 1 h / 20 °C

4: palladium 10% on activated carbon; triethylamine; hydrogen / methanol; tetrahydrofuran / 18 h / 20 °C

5: pyridine; bromine / chloroform / 0.17 h / 0 - 20 °C

6: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / 1-methyl-pyrrolidin-2-one / 3.5 h / 100 °C / Inert atmosphere

7: sodium methylate / methanol; tetrahydrofuran / 1 h / 20 °C

With pyridine; triethylsilane; dmap; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; methanesulfonic acid; palladium 10% on activated carbon; boron trifluoride diethyl etherate; hydrogen; bromine; sodium methylate; triethylamine; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; methanol; hexane; dichloromethane; chloroform; toluene;
DOI:10.1016/j.bmc.2013.05.048