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

Base Information

• Chemical Name: 2-(p-iodophenyl)ethyl 2,3,4-tri-O-acetyl-6-O-allyloxycarbonyl-β-D-glucopyranoside
• CAS No.: 1357000-54-4
• Molecular Formula: C₂₄H₂₉IO₁₁
• Molecular Weight: 620.392
• Mol file: 1357000-54-4.mol

Synonyms:2-(p-iodophenyl)ethyl 2,3,4-tri-O-acetyl-6-O-allyloxycarbonyl-β-D-glucopyranoside

Chemical Property of 2-(p-iodophenyl)ethyl 2,3,4-tri-O-acetyl-6-O-allyloxycarbonyl-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(p-iodophenyl)ethyl 2,3,4-tri-O-acetyl-6-O-allyloxycarbonyl-β-D-glucopyranoside

There total 1 articles about 2-(p-iodophenyl)ethyl 2,3,4-tri-O-acetyl-6-O-allyloxycarbonyl-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: 62.0%

4-iodophenethyl alcohol (52914-23-5) + C18H22Cl3NO11 → 2-(p-iodophenyl)ethyl 2,3,4-tri-O-acetyl-6-O-allyloxycarbonyl-β-D-glucopyranoside (1357000-54-4)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -20 ℃; for 4h;

DOI:10.3987/COM-11-12332

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-(p-iodophenyl)ethyl 2,3,4-tri-O-acetyl-6-O-allyloxycarbonyl-β-D-glucopyranoside (1357000-54-4) → 2-(p-iodophenyl)ethyl 2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->2)-α-D-mannopyranosyl-(1->6)-β-D-glucopyranoside (865488-97-7)

Guidance literature:

Multi-step reaction with 3 steps

1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; formic acid; triphenylphosphine / tetrahydrofuran / 1 h

2: N-iodo-succinimide; trifluorormethanesulfonic acid / dichloromethane / 2.5 h / -50 °C / Molecular sieve

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

With methanol; N-iodo-succinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; formic acid; trifluorormethanesulfonic acid; sodium methylate; triphenylphosphine; In tetrahydrofuran; dichloromethane;

DOI:10.3987/COM-11-12332

upstream raw materials:

4-iodophenethyl alcohol

Downstream raw materials:

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

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