phenyl 2,3,4-tri-O-acethyl-6-O-[methyl-O-(6-O-tert-butyldiphenylsilyl-α-D-mannopyranos-3-yloxy)-2-carbonylbenzoyl]-1-thio-α-D-mannopyranoside

Base Information

• Chemical Name: phenyl 2,3,4-tri-O-acethyl-6-O-[methyl-O-(6-O-tert-butyldiphenylsilyl-α-D-mannopyranos-3-yloxy)-2-carbonylbenzoyl]-1-thio-α-D-mannopyranoside
• CAS No.: 858106-57-7
• Molecular Formula: C₄₉H₅₆O₁₆SSi
• Molecular Weight: 961.126
• Mol file: 858106-57-7.mol

Synonyms:phenyl 2,3,4-tri-O-acethyl-6-O-[methyl-O-(6-O-tert-butyldiphenylsilyl-α-D-mannopyranos-3-yloxy)-2-carbonylbenzoyl]-1-thio-α-D-mannopyranoside

Chemical Property of phenyl 2,3,4-tri-O-acethyl-6-O-[methyl-O-(6-O-tert-butyldiphenylsilyl-α-D-mannopyranos-3-yloxy)-2-carbonylbenzoyl]-1-thio-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 2,3,4-tri-O-acethyl-6-O-[methyl-O-(6-O-tert-butyldiphenylsilyl-α-D-mannopyranos-3-yloxy)-2-carbonylbenzoyl]-1-thio-α-D-mannopyranoside

There total 4 articles about phenyl 2,3,4-tri-O-acethyl-6-O-[methyl-O-(6-O-tert-butyldiphenylsilyl-α-D-mannopyranos-3-yloxy)-2-carbonylbenzoyl]-1-thio-α-D-mannopyranoside 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: 52.0%

3-O-benzoyl-6-O-(t-butyldiphenyl)silyl-α-D-mannopyranoside (131089-34-4) + 2-Chlorocarbonyl-benzoic acid (2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl ester (288104-41-6) → phenyl 2,3,4-tri-O-acethyl-6-O-[methyl-O-(6-O-tert-butyldiphenylsilyl-α-D-mannopyranos-3-yloxy)-2-carbonylbenzoyl]-1-thio-α-D-mannopyranoside (858106-57-7)

Guidance literature:

3-O-benzoyl-6-O-(t-butyldiphenyl)silyl-α-D-mannopyranoside; With di(n-butyl)tin oxide; In toluene; for 0.0333333h; Heating; microwave irradiation;

2-Chlorocarbonyl-benzoic acid (2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl ester; In toluene; at 20 ℃; for 20h;

DOI:10.1055/s-2005-865228

Reference yield:

Phthalic acid mono-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl) ester; compound with triethyl-amine → phenyl 2,3,4-tri-O-acethyl-6-O-[methyl-O-(6-O-tert-butyldiphenylsilyl-α-D-mannopyranos-3-yloxy)-2-carbonylbenzoyl]-1-thio-α-D-mannopyranoside (858106-57-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: SOCl₂; DMF / toluene / 4 h / Heating

2.1: n-Bu₂SnO / toluene / 0.03 h / Heating; microwave irradiation

2.2: 52 percent / toluene / 20 h / 20 °C

With thionyl chloride; di(n-butyl)tin oxide; N,N-dimethyl-formamide; In toluene;

DOI:10.1055/s-2005-865228

Reference yield:

phthalic anhydride (85-44-9) → phenyl 2,3,4-tri-O-acethyl-6-O-[methyl-O-(6-O-tert-butyldiphenylsilyl-α-D-mannopyranos-3-yloxy)-2-carbonylbenzoyl]-1-thio-α-D-mannopyranoside (858106-57-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 80 percent / CH₂Cl₂ / 4 h / 20 °C

2.1: SOCl₂; DMF / toluene / 4 h / Heating

3.1: n-Bu₂SnO / toluene / 0.03 h / Heating; microwave irradiation

3.2: 52 percent / toluene / 20 h / 20 °C

With thionyl chloride; di(n-butyl)tin oxide; N,N-dimethyl-formamide; In dichloromethane; toluene;

DOI:10.1055/s-2005-865228

upstream raw materials:

3-O-benzoyl-6-O-(t-butyldiphenyl)silyl-α-D-mannopyranoside

2-Chlorocarbonyl-benzoic acid (2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl ester

phthalic anhydride

phenyl 2,3,4-tri-O-acetyl-1-thio-α-D-mannopyranoside

Downstream raw materials:

C₄₃H₅₀O₁₆Si

C₄₃H₅₀O₁₆Si