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

Base Information

Chemical Name:3-[(5-chloro-2-thienyl)methyl]-4-methyl-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)benzene
CAS No.:842133-87-3
Molecular Formula:C₂₆H₂₉ClO₉S
Molecular Weight:553.03
Hs Code.:

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

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Chemical Property of 3-[(5-chloro-2-thienyl)methyl]-4-methyl-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)benzene

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Technology Process of 3-[(5-chloro-2-thienyl)methyl]-4-methyl-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)benzene

There total 7 articles about 3-[(5-chloro-2-thienyl)methyl]-4-methyl-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)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: 75.0%

: 842132-58-5
3-[(5-chloro-2-thienyl)methyl]-1-(β-D-glucopyranosyl)-4-methylbenzene

: 108-24-7
acetic anhydride

: 842133-87-3
3-[(5-chloro-2-thienyl)methyl]-4-methyl-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)benzene

Guidance literature:: With pyridine; dmap; In chloroform; at 20 ℃; for 1h;
DOI:10.1016/j.bmc.2013.05.048

Reference yield:

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

: 842133-87-3
3-[(5-chloro-2-thienyl)methyl]-4-methyl-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)benzene

Guidance literature:: Multi-step reaction with 6 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

With pyridine; triethylsilane; dmap; aluminum (III) chloride; n-butyllithium; methanesulfonic acid; boron trifluoride diethyl etherate; In tetrahydrofuran; hexane; dichloromethane; chloroform; toluene; acetonitrile; 3.2: |Barbier Coupling Reaction;
DOI:10.1016/j.bmc.2013.05.048

Reference yield:

: C₃₀H₅₃ClO₆SSi₄

: 842133-87-3
3-[(5-chloro-2-thienyl)methyl]-4-methyl-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)benzene

Guidance literature:: Multi-step reaction with 3 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

With pyridine; triethylsilane; dmap; methanesulfonic acid; boron trifluoride diethyl etherate; In tetrahydrofuran; hexane; dichloromethane; chloroform; toluene;
DOI:10.1016/j.bmc.2013.05.048