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

Base Information

• Chemical Name: phenyl 2-azido-3-O-benzyl-2-deoxy-1-thio-α-D-mannopyranosiduronic acid
• CAS No.: 928260-35-9
• Molecular Formula: C₁₉H₁₉N₃O₅S
• Molecular Weight: 401.443
• Mol file: 928260-35-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 8 articles about phenyl 2-azido-3-O-benzyl-2-deoxy-1-thio-α-D-mannopyranosiduronic acid 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: 65.0%

phenyl 2-azido-3-O-benzyl-2-deoxy-1-thio-α-D-mannopyranoside (930576-68-4) → phenyl 2-azido-3-O-benzyl-2-deoxy-1-thio-α-D-mannopyranosiduronic acid (928260-35-9)

Guidance literature:

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene; In dichloromethane; water;

DOI:10.1002/ejoc.200600759

Reference yield:

7-azido-2-phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol → phenyl 2-azido-3-O-benzyl-2-deoxy-1-thio-α-D-mannopyranosiduronic acid (928260-35-9)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium hydride / dimethylformamide / 0 °C

2: p-toluenesulfonic acid hydrate / methanol / 1 h / Heating

3: 65 percent / TEMPO; BAIB / CH₂Cl₂; H₂O

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene; sodium hydride; toluene-4-sulfonic acid; In methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1002/ejoc.200600759

Reference yield:

7-azido-8-benzyloxy-2-phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxine → phenyl 2-azido-3-O-benzyl-2-deoxy-1-thio-α-D-mannopyranosiduronic acid (928260-35-9)

Guidance literature:

Multi-step reaction with 2 steps

1: p-toluenesulfonic acid hydrate / methanol / 1 h / Heating

2: 65 percent / TEMPO; BAIB / CH₂Cl₂; H₂O

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene; toluene-4-sulfonic acid; In methanol; dichloromethane; water;

DOI:10.1002/ejoc.200600759

upstream raw materials:

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

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

phenyl 2-azido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-α-D-mannopyranoside

phenyl 4,6-di-O-acetyl-2-azido-3-O-benzyl-2-deoxy-1-thio-α-D-mannopyranoside

Downstream raw materials:

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

methyl (phenyl 4-O-acetyl-2-azido-3-O-benzyl-2-deoxy-1-thio-α-D-mannopyranosyl uronate)

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

3-O-(6-O-methyl-6-oxy-4-O-acetyl-2-azido-3-O-benzyl-2-deoxy-β-D-mannopyranosyl)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose