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

Base Information

• Chemical Name: methyl (phenyl 2-azido-3-O-benzyl-2-deoxy-1-thio-α-D-mannopyranosyl uronate)
• CAS No.: 928260-36-0
• Molecular Formula: C₂₀H₂₁N₃O₅S
• Molecular Weight: 415.47
• Mol file: 928260-36-0.mol

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

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

There total 9 articles about methyl (phenyl 2-azido-3-O-benzyl-2-deoxy-1-thio-α-D-mannopyranosyl 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: 71.0%

phenyl 2-azido-3-O-benzyl-2-deoxy-1-thio-α-D-mannopyranosiduronic acid (928260-35-9) + methyl iodide (74-88-4) → methyl (phenyl 2-azido-3-O-benzyl-2-deoxy-1-thio-α-D-mannopyranosyl uronate) (928260-36-0)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide;

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-α-D-mannopyranosyl uronate) (928260-36-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 65 percent / TEMPO; BAIB / CH₂Cl₂; H₂O

2: 71 percent / K₂CO₃ / dimethylformamide

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

DOI:10.1002/ejoc.200600759

Reference yield:

7-azido-2-phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol → methyl (phenyl 2-azido-3-O-benzyl-2-deoxy-1-thio-α-D-mannopyranosyl uronate) (928260-36-0)

Guidance literature:

Multi-step reaction with 4 steps

1: sodium hydride / dimethylformamide / 0 °C

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

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

4: 71 percent / K₂CO₃ / dimethylformamide

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

DOI:10.1002/ejoc.200600759

upstream raw materials:

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

methyl iodide

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

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

Downstream raw materials:

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

C₁₇H₁₈⁽²⁾H₃N₃O₇

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