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

Base Information

• Chemical Name: 2-(4-iodophenyl)ethyl 6-O-[2,6-di-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-α-D-mannopyranosyl]-β-D-glucopyranoside
• CAS No.: 865489-05-0
• Molecular Formula: C₃₆H₅₅IN₂O₂₁
• Molecular Weight: 978.738
• Mol file: 865489-05-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 22 articles about 2-(4-iodophenyl)ethyl 6-O-[2,6-di-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-α-D-mannopyranosyl]-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: 57.0%

2-(4-iodophenyl)ethyl 6-O-[2,6-di-O-(3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-β-D-glucopyranosyl)-3,4-di-O-acetyl-α-D-mannopyranosyl]-2,3,4-tri-O-acetyl-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 (865489-05-0)

Guidance literature:

With methanol; sodium methylate; at 20 ℃; for 0.5h;

DOI:10.1016/j.bmc.2011.05.047

Reference yield:

2,3,4-tri-O-acetyl-6-O-allyloxycarbonyl-α-D-glucopyranosyl trichloroacetimidate (1323156-29-1) → 2-(4-iodophenyl)ethyl 6-O-[2,6-di-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-α-D-mannopyranosyl]-β-D-glucopyranoside (865489-05-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: boron trifluoride diethyl etherate / dichloromethane / 2 h / -20 °C

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

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

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

4.2: 2 h / 0 °C / Inert atmosphere

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

6.1: silver perchlorate; silver carbonate / dichloromethane; toluene / 15 h

7.1: methanol; sodium methylate / 0.5 h / 20 °C

With methanol; tetrakis(triphenylphosphine) palladium⁽⁰⁾; formic acid; boron trifluoride diethyl etherate; sodium methylate; bis(tri-n-butyltin); silver perchlorate; pyridinium p-toluenesulfonate; triphenylphosphine; silver carbonate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/j.bmc.2011.05.047

Reference yield:

2-(4-bromophenyl)ethyl 2,3,4-tri-O-acetyl-β-D-glucopyranoside (865488-89-7) → 2-(4-iodophenyl)ethyl 6-O-[2,6-di-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-α-D-mannopyranosyl]-β-D-glucopyranoside (865489-05-0)

Guidance literature:

Multi-step reaction with 5 steps

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

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

2.2: 2 h / 0 °C / Inert atmosphere

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

4.1: silver perchlorate; silver carbonate / dichloromethane; toluene / 15 h

5.1: methanol; sodium methylate / 0.5 h / 20 °C

With methanol; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium methylate; bis(tri-n-butyltin); silver perchlorate; pyridinium p-toluenesulfonate; triphenylphosphine; silver carbonate; In methanol; dichloromethane; N,N-dimethyl-formamide; toluene;

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