S-phenyl 2,3-O-carbonyl-4,6-O-benzylidene-1-thia-α-D-mannopyranoside

Base Information

• Chemical Name: S-phenyl 2,3-O-carbonyl-4,6-O-benzylidene-1-thia-α-D-mannopyranoside
• CAS No.: 263543-67-5
• Molecular Formula: C₂₀H₁₈O₆S
• Molecular Weight: 386.425
• Mol file: 263543-67-5.mol

Synonyms:S-phenyl 2,3-O-carbonyl-4,6-O-benzylidene-1-thia-α-D-mannopyranoside

Chemical Property of S-phenyl 2,3-O-carbonyl-4,6-O-benzylidene-1-thia-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of S-phenyl 2,3-O-carbonyl-4,6-O-benzylidene-1-thia-α-D-mannopyranoside

There total 1 articles about S-phenyl 2,3-O-carbonyl-4,6-O-benzylidene-1-thia-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: 87.0%

phosgene (75-44-5) + phenyl 4,6-O-benzylidene-1-thio-α-D-mannopyranoside (159407-19-9) → S-phenyl 2,3-O-carbonyl-4,6-O-benzylidene-1-thia-α-D-mannopyranoside (263543-67-5)

Guidance literature:

With pyridine; In hexane; at 0 ℃; for 0.166667h;

DOI:10.1021/jo9910482

Reference yield: 65.0%

methyl 2,4-di-O-benzyl-α-D-mannopyranoside (58341-67-6,67381-34-4,86172-91-0,86342-19-0,67381-29-7) + S-phenyl 2,3-O-carbonyl-4,6-O-benzylidene-1-thia-α-D-mannopyranoside (263543-67-5) → 2,4-di-O-benzyl-3-O-(2,3-O-carbonyl-4,6-O-benzylidene-α-D-mannopyranosyl)-6-O-(2,3-O-carbonyl-4,6-O-benzylidene-α-D-mannopyranosyl)-α-D-mannoside

Guidance literature:

S-phenyl 2,3-O-carbonyl-4,6-O-benzylidene-1-thia-α-D-mannopyranoside; With 1-benzenesulfinyl piperidine; trifluoromethylsulfonic anhydride; 2,4,6-tri-tert-butylpyrimidine; In dichloromethane; at -60 ℃; for 0.0833333h; molecular sievs;

methyl 2,4-di-O-benzyl-α-D-mannopyranoside; In dichloromethane; at -60 - 20 ℃;

Reference yield:

trifluoromethylsulfonic anhydride (358-23-6) + S-phenyl 2,3-O-carbonyl-4,6-O-benzylidene-1-thia-α-D-mannopyranoside (263543-67-5) → Trifluoro-methanesulfonic acid (3aS,4R,5aR,8R,9aR,9bS)-2-oxo-8-phenyl-hexahydro-[1,3]dioxolo[4',5':4,5]pyrano[3,2-d][1,3]dioxin-4-yl ester

Guidance literature:

With 1-benzenesulfinyl piperidine; 3 A molecular sieve; In dichloromethane; at -60 ℃; for 0.0833333h;

DOI:10.1021/ja0111481

upstream raw materials:

phosgene

phenyl 4,6-O-benzylidene-1-thio-α-D-mannopyranoside

Downstream raw materials:

6-O-[4,6-O-benzylidene-α-D-mannopyranosyl]-1,2:3,4-di-O-isopropylidene-α-D-galactopyranoside

6-O-[2,3-O-carbonyl-4,6-O-benzylidene-α-D-mannopyranosyl]-1,2:3,4-di-O-isopropylidene-α-D-galactopyranoside