phenyl 3-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: phenyl 3-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-glucopyranoside
• CAS No.: 535961-73-0
• Molecular Formula: C₅₃H₄₅N₃O₁₃S
• Molecular Weight: 964.019

Synonyms:phenyl 3-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-glucopyranoside

Chemical Property of phenyl 3-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

Technology Process of phenyl 3-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-glucopyranoside

There total 3 articles about phenyl 3-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-2-azido-4,6-O-benzylidene-2-deoxy-1-thio-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: 64.0%

phenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-glucopyranoside (277756-84-0) + phenyl (2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->3)-4-O-acetyl-2,6-di-O-benzoyl-1-thio-β-D-galactopyranoside (548477-85-6) → phenyl 3-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-glucopyranoside (535961-73-0)

Guidance literature:

phenyl (2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->3)-4-O-acetyl-2,6-di-O-benzoyl-1-thio-β-D-galactopyranoside; With 1-benzenesulfinyl piperidine; trifluoromethanesulfonic acid anhydride; 2,4,6-tri-tert-butylpyrimidine; In dichloromethane; at -60 ℃; for 0.0833333h;

phenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-glucopyranoside; In dichloromethane; at -60 - -10 ℃; Further stages.;

DOI:10.1016/j.tet.2003.11.084

Reference yield:

phenyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-galactopyranoside (62774-33-8,65236-83-1,65236-84-2,65236-86-4,121523-94-2,121523-99-7,121524-00-3,65615-60-3) + phenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-glucopyranoside (277756-84-0) → phenyl 3-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-glucopyranoside (535961-73-0)

Guidance literature:

phenyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-galactopyranoside; With 1-benzenesulfinyl piperidine; 2,4,5-tri-tert-butylpyrimidine; trifluoromethanesulfonic acid anhydride; In dichloromethane; at -60 ℃; for 0.0833333h;

phenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-glucopyranoside; In dichloromethane; at -60 - -10 ℃;

DOI:10.1021/ol034312t

Reference yield:

phenyl 4-O-acetyl-2,6-di-O-benzoyl-1-thio-β-thio-β-D-galactopyranoside (152488-28-3) → phenyl 3-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-glucopyranoside (535961-73-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 2,4,6-tri-tert-butylpyrimidine; 1-benzenesulfinyl piperidine; trifluoromethanesulfonic anhydride / CH₂Cl₂ / 0.08 h / -60 °C

1.2: 52 percent / CH₂Cl₂ / -60 - -10 °C

2.1: 2,4,6-tri-tert-butylpyrimidine; 1-benzenesulfinyl piperidine; trifluoromethanesulfonic anhydride / CH₂Cl₂ / 0.08 h / -60 °C

2.2: 64 percent / CH₂Cl₂ / -60 - -10 °C

With 1-benzenesulfinyl piperidine; trifluoromethanesulfonic acid anhydride; 2,4,6-tri-tert-butylpyrimidine; In dichloromethane;

DOI:10.1016/j.tet.2003.11.084

upstream raw materials:

phenyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-galactopyranoside

phenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-glucopyranoside

phenyl (2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->3)-4-O-acetyl-2,6-di-O-benzoyl-1-thio-β-D-galactopyranoside

phenyl 4-O-acetyl-2,6-di-O-benzoyl-1-thio-β-thio-β-D-galactopyranoside

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