methyl [phenyl 2-azido-3-O-benzyl-2-deoxy-1-thio-4-O-(4-azido-2,3-di-O-benzyl-4-deoxy-α-D-fucopyranosyl)-α-D-mannopyranosid]uronate

Base Information

• Chemical Name: methyl [phenyl 2-azido-3-O-benzyl-2-deoxy-1-thio-4-O-(4-azido-2,3-di-O-benzyl-4-deoxy-α-D-fucopyranosyl)-α-D-mannopyranosid]uronate
• CAS No.: 928260-50-8
• Molecular Formula: C₄₀H₄₂N₆O₈S
• Molecular Weight: 766.875
• Mol file: 928260-50-8.mol

Synonyms:methyl [phenyl 2-azido-3-O-benzyl-2-deoxy-1-thio-4-O-(4-azido-2,3-di-O-benzyl-4-deoxy-α-D-fucopyranosyl)-α-D-mannopyranosid]uronate

Chemical Property of methyl [phenyl 2-azido-3-O-benzyl-2-deoxy-1-thio-4-O-(4-azido-2,3-di-O-benzyl-4-deoxy-α-D-fucopyranosyl)-α-D-mannopyranosid]uronate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl [phenyl 2-azido-3-O-benzyl-2-deoxy-1-thio-4-O-(4-azido-2,3-di-O-benzyl-4-deoxy-α-D-fucopyranosyl)-α-D-mannopyranosid]uronate

There total 8 articles about methyl [phenyl 2-azido-3-O-benzyl-2-deoxy-1-thio-4-O-(4-azido-2,3-di-O-benzyl-4-deoxy-α-D-fucopyranosyl)-α-D-mannopyranosid]uronate 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: 67.0%

4-azido-2,3-di-O-benzyl-4-deoxy-α/b-D-fucopyranose + methyl (phenyl 2-azido-3-O-benzyl-2-deoxy-1-thio-α-D-mannopyranosyl uronate) (928260-36-0) → methyl [phenyl 2-azido-3-O-benzyl-2-deoxy-1-thio-4-O-(4-azido-2,3-di-O-benzyl-4-deoxy-α-D-fucopyranosyl)-α-D-mannopyranosid]uronate (928260-50-8)

Guidance literature:

4-azido-2,3-di-O-benzyl-4-deoxy-α/b-D-fucopyranose; With 1,1'-sulfinylbisbenzene; 2,4,6-tri-tert-butylpyrimidine; In dichloromethane; for 0.5h;

methyl (phenyl 2-azido-3-O-benzyl-2-deoxy-1-thio-α-D-mannopyranosyl uronate); With trifluoromethylsulfonic anhydride; In dichloromethane; at -40 - 0 ℃;

DOI:10.1002/ejoc.200600759

Reference yield: 55.0%

methyl (phenyl 2-azido-3-O-benzyl-2-deoxy-1-thio-α-D-mannopyranosyl uronate) (928260-36-0) + phenyl 2,3-di-O-benzyl-4-azido-4,6-dideoxy-1-thio-β-D-galactopyranoside → methyl [phenyl 2-azido-3-O-benzyl-2-deoxy-1-thio-4-O-(4-azido-2,3-di-O-benzyl-4-deoxy-α-D-fucopyranosyl)-α-D-mannopyranosid]uronate (928260-50-8)

Guidance literature:

(2R,3S,4S,5R,6S)-3-Azido-4,5-bis-benzyloxy-2-methyl-6-phenylsulfanyl-tetrahydro-pyran; With 1,1'-sulfinylbisbenzene; 2,4,6-tri-tert-butylpyrimidine; In dichloromethane; for 0.5h;

methyl (phenyl 2-azido-3-O-benzyl-2-deoxy-1-thio-α-D-mannopyranosyl uronate); With trifluoromethylsulfonic anhydride; In dichloromethane; at -50 - 20 ℃;

DOI:10.1002/ejoc.200600759

Reference yield:

phenyl 2-azido-3-O-benzyl-2-deoxy-1-thio-α-D-mannopyranoside (930576-68-4) → methyl [phenyl 2-azido-3-O-benzyl-2-deoxy-1-thio-4-O-(4-azido-2,3-di-O-benzyl-4-deoxy-α-D-fucopyranosyl)-α-D-mannopyranosid]uronate (928260-50-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 65 percent / TEMPO; BAIB / CH₂Cl₂; H₂O

2.1: 71 percent / K₂CO₃ / dimethylformamide

3.1: diphenyl sulfoxide; 2,4,6-tri-tert-butylpyrimidine / CH₂Cl₂ / 0.5 h

3.2: 67 percent / triflic anhydride / CH₂Cl₂ / -40 - 0 °C

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene; 1,1'-sulfinylbisbenzene; potassium carbonate; 2,4,6-tri-tert-butylpyrimidine; In dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1002/ejoc.200600759

upstream raw materials:

methyl (phenyl 2-azido-3-O-benzyl-2-deoxy-1-thio-α-D-mannopyranosyl uronate)

phenyl 2-azido-3-O-benzyl-2-deoxy-1-thio-α-D-mannopyranoside

phenyl 2-azido-3-O-benzyl-2-deoxy-1-thio-α-D-mannopyranosiduronic acid

phenyl 2-azido-2-deoxy-1-thio-α-D-mannopyranoside