p-chlorophenyl 2-acetamido-3-O-acetyl-2-deoxy-4,6-di-O-pivaloyl-1-thio-β-D-galactopyranoside

Base Information

• Chemical Name: p-chlorophenyl 2-acetamido-3-O-acetyl-2-deoxy-4,6-di-O-pivaloyl-1-thio-β-D-galactopyranoside
• CAS No.: 1258839-49-4
• Molecular Formula: C₂₆H₃₆ClNO₈S
• Molecular Weight: 558.093
• Mol file: 1258839-49-4.mol

Synonyms:p-chlorophenyl 2-acetamido-3-O-acetyl-2-deoxy-4,6-di-O-pivaloyl-1-thio-β-D-galactopyranoside

Chemical Property of p-chlorophenyl 2-acetamido-3-O-acetyl-2-deoxy-4,6-di-O-pivaloyl-1-thio-β-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of p-chlorophenyl 2-acetamido-3-O-acetyl-2-deoxy-4,6-di-O-pivaloyl-1-thio-β-D-galactopyranoside

There total 1 articles about p-chlorophenyl 2-acetamido-3-O-acetyl-2-deoxy-4,6-di-O-pivaloyl-1-thio-β-D-galactopyranoside 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:

2-acetamido-3-O-acetyl-2-deoxy-4,6-di-O-pivaloyl-α-D-galactopyranosyl chloride (1258839-47-2) + p-Chlorothiophenol (106-54-7) → p-chlorophenyl 2-acetamido-3-O-acetyl-2-deoxy-4,6-di-O-pivaloyl-1-thio-β-D-galactopyranoside (1258839-49-4)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1016/j.carres.2010.09.008

Reference yield: 94.1%

p-chlorophenyl 2-acetamido-3-O-acetyl-2-deoxy-4,6-di-O-pivaloyl-1-thio-β-D-galactopyranoside (1258839-49-4) → p-chlorophenyl 2-amino-2-deoxy-1-thio-β-D-galactopyranoside (1352306-62-7)

Guidance literature:

p-chlorophenyl 2-acetamido-3-O-acetyl-2-deoxy-4,6-di-O-pivaloyl-1-thio-β-D-galactopyranoside; With sodium hydroxide; In water; Reflux;

With hydrogenchloride; In water; pH=8;

DOI:10.1016/j.carres.2011.09.015

Reference yield:

p-chlorophenyl 2-acetamido-3-O-acetyl-2-deoxy-4,6-di-O-pivaloyl-1-thio-β-D-galactopyranoside (1258839-49-4) → p-chlorophenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl-(1->3)-4,6-O-benzylidene-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-1-thio-β-D-galactopyranoside (1352307-19-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: sodium hydroxide / water / Reflux

1.2: pH 8

2.1: pyridine; triflic azide; copper(II) sulfate / 7 h / 0 - 20 °C

3.1: pyridine / 20 °C

4.1: N-iodo-succinimide / water; acetonitrile

5.1: potassium carbonate / dichloromethane

6.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / -78 - 0 °C / Molecular sieve

With pyridine; N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; triflic azide; potassium carbonate; copper(II) sulfate; sodium hydroxide; In dichloromethane; water; acetonitrile;

DOI:10.1016/j.carres.2011.09.015

upstream raw materials:

2-acetamido-3-O-acetyl-2-deoxy-4,6-di-O-pivaloyl-α-D-galactopyranosyl chloride

p-Chlorothiophenol

Downstream raw materials:

p-chlorophenyl 4,6-O-benzylidene-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-1-thio-β-D-galactopyranoside

p-chlorophenyl 2-amino-2-deoxy-1-thio-β-D-galactopyranoside

p-chlorophenyl 2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-1-thio-β-D-galactopyranoside

p-chlorophenyl 3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-1-thio-β-D-galactopyranoside