phenyl 2,4-di-O-benzoyl-3-O-chloroacetyl-6-O-levulinoyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-1-thio-β-D-galactopyranoside

Base Information

• Chemical Name: phenyl 2,4-di-O-benzoyl-3-O-chloroacetyl-6-O-levulinoyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-1-thio-β-D-galactopyranoside
• CAS No.: 821018-26-2
• Molecular Formula: C₆₀H₅₃ClO₁₈S
• Molecular Weight: 1129.59

Synonyms:phenyl 2,4-di-O-benzoyl-3-O-chloroacetyl-6-O-levulinoyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-1-thio-β-D-galactopyranoside

Chemical Property of phenyl 2,4-di-O-benzoyl-3-O-chloroacetyl-6-O-levulinoyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-1-thio-β-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 2,4-di-O-benzoyl-3-O-chloroacetyl-6-O-levulinoyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-1-thio-β-D-galactopyranoside

There total 8 articles about phenyl 2,4-di-O-benzoyl-3-O-chloroacetyl-6-O-levulinoyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-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: 100.0%

phenyl 2,3,4-tri-O-benzoyl-1-thio-β-D-galactopyranoside (139608-11-0) + 2,4-di-O-benzoyl-3-chloroacetyl-6-O-levulinoyl-α-D-galactopyranosyl trichloroacetimidate (821018-24-0) → phenyl 2,4-di-O-benzoyl-3-O-chloroacetyl-6-O-levulinoyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-1-thio-β-D-galactopyranoside (821018-26-2)

Guidance literature:

phenyl 2,3,4-tri-O-benzoyl-1-thio-β-D-galactopyranoside; 2,4-di-O-benzoyl-3-chloroacetyl-6-O-levulinoyl-α-D-galactopyranosyl trichloroacetimidate; In dichloromethane; at 20 ℃; for 2h;

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0 ℃; for 0.5h;

DOI:10.1016/j.carres.2004.09.015

Reference yield:

2-(trimethylsilyl)ethyl β-D-galactopyranoside (117252-95-6) → phenyl 2,4-di-O-benzoyl-3-O-chloroacetyl-6-O-levulinoyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-1-thio-β-D-galactopyranoside (821018-26-2)

Guidance literature:

Multi-step reaction with 8 steps

1.1: dibutyltin oxide / benzene / 5 h / Heating

1.2: 100 percent / Bu₄NBr / benzene / 4.5 h

2.1: 87.7 percent / DCC; DMAP / CH₂Cl₂ / 3 h / 20 °C

3.1: 82 percent / pyridine / 2 h

4.1: 100 percent / H₂ / Pd-C / tetrahydrofuran; methanol / 4 h / 20 °C

5.1: 89.7 percent / pyridine; CH₂Cl₂ / 2 h / 20 °C

6.1: CF₃COOH / CH₂Cl₂ / 2 h / 20 °C

7.1: 66 mg / DBU / CH₂Cl₂ / 1 h / 0 °C

8.1: 4A MS / CH₂Cl₂ / 2 h / 20 °C

8.2: 100 percent / TMSOTf / CH₂Cl₂ / 0.5 h / 0 °C

With dmap; hydrogen; di(n-butyl)tin oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; dichloromethane; benzene;

DOI:10.1016/j.carres.2004.09.015

Reference yield:

2-(trimethylsilyl)ethyl 3-O-benzyl-β-D-galactopyranoside (121360-14-3) → phenyl 2,4-di-O-benzoyl-3-O-chloroacetyl-6-O-levulinoyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-1-thio-β-D-galactopyranoside (821018-26-2)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 87.7 percent / DCC; DMAP / CH₂Cl₂ / 3 h / 20 °C

2.1: 82 percent / pyridine / 2 h

3.1: 100 percent / H₂ / Pd-C / tetrahydrofuran; methanol / 4 h / 20 °C

4.1: 89.7 percent / pyridine; CH₂Cl₂ / 2 h / 20 °C

5.1: CF₃COOH / CH₂Cl₂ / 2 h / 20 °C

6.1: 66 mg / DBU / CH₂Cl₂ / 1 h / 0 °C

7.1: 4A MS / CH₂Cl₂ / 2 h / 20 °C

7.2: 100 percent / TMSOTf / CH₂Cl₂ / 0.5 h / 0 °C

With dmap; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; dichloromethane;

DOI:10.1016/j.carres.2004.09.015

upstream raw materials:

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

2,4-di-O-benzoyl-3-chloroacetyl-6-O-levulinoyl-α-D-galactopyranosyl trichloroacetimidate

2-(trimethylsilyl)ethyl β-D-galactopyranoside

2-(trimethylsilyl)ethyl 3-O-benzyl-β-D-galactopyranoside

Downstream raw materials:

phenyl 2,4-di-O-benzoyl-6-O-levulinoyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-1-thio-β-D-galactopyranoside

phenyl 2,4-di-O-benzoyl-3-O-chloroacetyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-1-thio-β-D-galactopyranoside

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