p-tolyl 2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-galactopyranoside

Base Information

• Chemical Name: p-tolyl 2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-galactopyranoside
• CAS No.: 949489-15-0
• Molecular Formula: C₅₄H₅₃N₃O₁₀S
• Molecular Weight: 936.095
• Mol file: 949489-15-0.mol

Synonyms:p-tolyl 2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-galactopyranoside

Chemical Property of p-tolyl 2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of p-tolyl 2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-galactopyranoside

There total 13 articles about p-tolyl 2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-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: 85.0%

p-tolyl 2-O-benzoyl-3,4,6-tri-O-benzyl-1-thio-β-D-galactopyranoside (917592-29-1) + 4-methylphenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-galactopyranoside (125760-23-8) → p-tolyl 2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-galactopyranoside (949489-15-0)

Guidance literature:

p-tolyl 2-O-benzoyl-3,4,6-tri-O-benzyl-1-thio-β-D-galactopyranoside; With trifluoromethylsulfonic anhydride; 1,1'-sulfinylbisbenzene; In dichloromethane; at -72 ℃; for 0.25h; Molecular sieve; Inert atmosphere;

4-methylphenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-galactopyranoside; In dichloromethane; at -72 - -20 ℃; for 2h; Inert atmosphere;

DOI:10.1039/d1md00067e

Reference yield:

p-tolyl 2-O-benzoyl-3,4,6-tri-O-benzyl-1-thio-β-D-galactopyranoside (917592-29-1) + 4-methylphenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-galactopyranoside (125760-23-8) → p-tolyl 2-O-benzoyl-3,4,6-tri-O-benzyl-α-D-galactopyranosyl-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-galactopyranoside + p-tolyl 2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-galactopyranoside (949489-15-0)

Guidance literature:

p-tolyl 2-O-benzoyl-3,4,6-tri-O-benzyl-1-thio-β-D-galactopyranoside; With silver trifluoromethanesulfonate; In diethyl ether; dichloromethane; at -78 ℃; for 0.0833333h;

4-methylphenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-galactopyranoside; In diethyl ether; dichloromethane; at -78 - -10 ℃; for 2h; Further stages.;

DOI:10.1021/jo070585g

Reference yield:

p-tolyl 2-O-acetyl-3,4,6-tri-O-benzyl-1-thio-β-D-galactopyranoside (897364-02-2) → p-tolyl 2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-galactopyranoside (949489-15-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 92 percent / NaOMe / methanol; CH₂Cl₂ / 2 h / 20 °C

2.1: N,N-dimethylaminopyridine; pyridine / 4 h / 20 °C

3.1: AgOTf; p-tolylsulfanyl chloride / CH₂Cl₂; diethyl ether / 0.08 h / -78 °C

3.2: CH₂Cl₂; diethyl ether / 2 h / -78 - -10 °C

With pyridine; dmap; sodium methylate; silver trifluoromethanesulfonate; In methanol; diethyl ether; dichloromethane;

DOI:10.1021/jo070585g

upstream raw materials:

p-tolyl 2-O-benzoyl-3,4,6-tri-O-benzyl-1-thio-β-D-galactopyranoside

4-methylphenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-galactopyranoside

p-tolyl 2-O-acetyl-3,4,6-tri-O-benzyl-1-thio-β-D-galactopyranoside

p-tolyl 3,4,6-tri-O-benzyl-1-thio-β-D-galactopyranoside

Downstream raw materials:

p-tolyl 3,4,6-tri-O-benzyl-β-D-galactopyranosyl-(1->3)-4,6-O-benzylidene-2-azido-2-deoxy-1-thio-β-D-galactopyranoside

p-tolyl 3,4,6-tri-O-benzyl-β-D-galactopyranosyl-(1->3)-4,6-O-benzylidene-2-amino-2-deoxy-1-thio-β-D-galactopyranoside

p-tolyl 3,4,6-tri-O-benzyl-β-D-galactopyranosyl-(1->3)-4,6-O-benzylidene-2-(2,2,2-trichloroethoxycarbonylamino)-2-deoxy-1-thio-β-D-galactopyranoside