2-(4-iodophenyl)ethyl 2,3,4-tri-O-acetyl-β-D-glucopyranoside

Base Information

• Chemical Name: 2-(4-iodophenyl)ethyl 2,3,4-tri-O-acetyl-β-D-glucopyranoside
• CAS No.: 865488-94-4
• Molecular Formula: C₂₀H₂₅IO₉
• Molecular Weight: 536.318
• Mol file: 865488-94-4.mol

Synonyms:2-(4-iodophenyl)ethyl 2,3,4-tri-O-acetyl-β-D-glucopyranoside

Chemical Property of 2-(4-iodophenyl)ethyl 2,3,4-tri-O-acetyl-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(4-iodophenyl)ethyl 2,3,4-tri-O-acetyl-β-D-glucopyranoside

There total 11 articles about 2-(4-iodophenyl)ethyl 2,3,4-tri-O-acetyl-β-D-glucopyranoside 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: 98.0%

2-(4-iodophenyl)ethyl 2,3,4-tri-O-acetyl-6-O-(1-ethoxyethyl)-β-D-glucopyranoside (865488-93-3) → 2-(4-iodophenyl)ethyl 2,3,4-tri-O-acetyl-β-D-glucopyranoside (865488-94-4)

Guidance literature:

With pyridinium p-toluenesulfonate; In methanol; at 55 ℃; for 2h;

DOI:10.1016/j.bmc.2011.05.047

Reference yield: 95.0%

2-(p-iodophenyl)ethyl 2,3,4-tri-O-acetyl-6-O-allyloxycarbonyl-β-D-glucopyranoside (1357000-54-4) → 2-(4-iodophenyl)ethyl 2,3,4-tri-O-acetyl-β-D-glucopyranoside (865488-94-4)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; formic acid; triphenylphosphine; In tetrahydrofuran; for 1h;

DOI:10.3987/COM-11-12332

Reference yield:

2-(4-bromophenyl)ethyl 2,3,4-tri-O-acetyl-6-O-allyloxycarbonyl-β-D-glucopyranoside (865488-88-6) → 2-(4-iodophenyl)ethyl 2,3,4-tri-O-acetyl-β-D-glucopyranoside (865488-94-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; formic acid; triphenylphosphine / tetrahydrofuran / 6 h / 20 °C / Inert atmosphere

2.1: pyridinium p-toluenesulfonate / dichloromethane / 1 h / 20 °C / Inert atmosphere

3.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; bis(tri-n-butyltin); triphenylphosphine / N,N-dimethyl-formamide / 4 h / 100 °C / Inert atmosphere

3.2: 2 h / 0 °C / Inert atmosphere

4.1: pyridinium p-toluenesulfonate / methanol / 2 h / 55 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; formic acid; bis(tri-n-butyltin); pyridinium p-toluenesulfonate; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2011.05.047

upstream raw materials:

1,2,3,4-tetra-O-acetyl-6-O-allyloxycarbonyl-β-D-glucopyranose

2,3,4-tri-O-acetyl-6-O-allyloxycarbonyl-α-D-glucopyranosyl trichloroacetimidate

2-(4-bromophenyl)ethyl 2,3,4-tri-O-acetyl-6-O-allyloxycarbonyl-β-D-glucopyranoside

2-(4-bromophenyl)ethyl 2,3,4-tri-O-acetyl-β-D-glucopyranoside

Downstream raw materials:

2-(p-iodophenyl)ethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1->2)-3,4,6-tri-O-acetyl-α-D-mannopyranosyl-(1->6)-2,3,4-tri-O-acetyl-β-D-glucopyranoside

2-(p-iodophenyl)ethyl 2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->2)-α-D-mannopyranosyl-(1->6)-β-D-glucopyranoside

2-(4-iodophenyl)ethyl 6-O-[2,6-di-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-α-D-mannopyranosyl]-β-D-glucopyranoside