S-phenyl 4,6-O-α-[2-(2-iodophenyl)ethylthiocarbonyl]benzylidene-2,3-di-O-benzyl-1-thio-α-D-mannopyranoside

Base Information

• Chemical Name: S-phenyl 4,6-O-α-[2-(2-iodophenyl)ethylthiocarbonyl]benzylidene-2,3-di-O-benzyl-1-thio-α-D-mannopyranoside
• CAS No.: 553663-21-1
• Molecular Formula: C₄₂H₃₉IO₆S₂
• Molecular Weight: 830.805
• Mol file: 553663-21-1.mol

Synonyms:S-phenyl 4,6-O-α-[2-(2-iodophenyl)ethylthiocarbonyl]benzylidene-2,3-di-O-benzyl-1-thio-α-D-mannopyranoside

Chemical Property of S-phenyl 4,6-O-α-[2-(2-iodophenyl)ethylthiocarbonyl]benzylidene-2,3-di-O-benzyl-1-thio-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of S-phenyl 4,6-O-α-[2-(2-iodophenyl)ethylthiocarbonyl]benzylidene-2,3-di-O-benzyl-1-thio-α-D-mannopyranoside

There total 1 articles about S-phenyl 4,6-O-α-[2-(2-iodophenyl)ethylthiocarbonyl]benzylidene-2,3-di-O-benzyl-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:

2-(2-iodophenyl)-1-ethanethiol (177748-62-8) + S-phenyl 4,6-O-α-(methoxycarbonyl)benzylidene-2,3-di-O-benzyl-1-thio-α-D-mannopyranoside → S-phenyl 4,6-O-α-[2-(2-iodophenyl)ethylthiocarbonyl]benzylidene-2,3-di-O-benzyl-1-thio-α-D-mannopyranoside (553663-00-6) + S-phenyl 4,6-O-α-[2-(2-iodophenyl)ethylthiocarbonyl]benzylidene-2,3-di-O-benzyl-1-thio-α-D-mannopyranoside (553663-21-1)

Guidance literature:

With trimethylaluminum; In hexane; toluene; for 4h; Heating;

DOI:10.1021/ol034741r

Reference yield: 77.0%

methyl 2,3,4-tri-O-benzyl-D-glucopyranoside (53008-65-4,641635-63-4) + S-phenyl 4,6-O-α-[2-(2-iodophenyl)ethylthiocarbonyl]benzylidene-2,3-di-O-benzyl-1-thio-α-D-mannopyranoside (553663-21-1) → methyl 2,3,4-tri-O-benzyl-6-O-{2,3-di-O-benzyl-4,6-O-[α-2-(2-iodophenyl)ethylthiocarbonyl]benzylidene-β-D-mannopyranosyl}-α-D-glucopyranoside (553663-11-9)

Guidance literature:

With 1-benzenesulfinyl piperidine; trifluoromethylsulfonic anhydride; 2,4,6-tri-tert-butylpyrimidine; molecular sieve; In dichloromethane; at -60 - 20 ℃; for 4h;

DOI:10.1021/ol034741r

Reference yield:

S-phenyl 4,6-O-α-[2-(2-iodophenyl)ethylthiocarbonyl]benzylidene-2,3-di-O-benzyl-1-thio-α-D-mannopyranoside (553663-21-1) → (2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl)-(1->6)-1-O-methyl-2,3,4-tri-O-benzoyl-α-D-glucopyranose

Guidance literature:

Multi-step reaction with 2 steps

1.1: 1-benzenesulfinylpiperidine; 2,4,6-tri-tert-butylpyrimidine; triflic anhydride / CH₂Cl₂ / 0.17 h / -60 °C

1.2: 77 percent / CH₂Cl₂ / 4 h / -60 - 20 °C

2.1: 8 percent / AIBN; Bu₃SnH / toluene / 4 h / Heating

With 1-benzenesulfinyl piperidine; 2,2'-azobis(isobutyronitrile); trifluoromethylsulfonic anhydride; tri-n-butyl-tin hydride; 2,4,6-tri-tert-butylpyrimidine; In dichloromethane; toluene;

DOI:10.1021/ja048070j

upstream raw materials:

2-(2-iodophenyl)-1-ethanethiol

Downstream raw materials:

methyl 2,3,4-tri-O-benzyl-6-O-{2,3-di-O-benzyl-4,6-O-[α-2-(2-iodophenyl)ethylthiocarbonyl]benzylidene-β-D-mannopyranosyl}-α-D-glucopyranoside