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

Base Information

• Chemical Name: 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
• CAS No.: 1185882-49-8
• Molecular Formula: C₂₈H₃₇N₃O₁₂
• Molecular Weight: 607.615
• Mol file: 1185882-49-8.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 13 articles about 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 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: 85.0%

methyl (phenyl 4-O-acetyl-2-azido-3-O-benzyl-2-deoxy-1-thio-β-D-mannopyranosyl uronate) (1185882-45-4) + 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (582-52-5) → 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 (1185882-49-8)

Guidance literature:

With trifluoromethylsulfonic anhydride; 1,1'-sulfinylbisbenzene; stereoselective reaction;

DOI:10.1016/j.carres.2010.02.027

Reference yield: 47.0%

methyl (phenyl 4-O-acetyl-2-azido-3-O-benzyl-2-deoxy-1-thio-α-D-mannopyranosyl uronate) (928260-37-1) + 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (582-52-5) → C25H33N3O12 + 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 (1185882-49-8)

Guidance literature:

methyl (phenyl 4-O-acetyl-2-azido-3-O-benzyl-2-deoxy-1-thio-α-D-mannopyranosyl uronate); With tri-tert-butyl phosphine; trifluoromethylsulfonic anhydride; 1,1'-sulfinylbisbenzene; In dichloromethane; at -65 - 55 ℃; for 0.25h; Inert atmosphere; Molecular sieve;

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose; In dichloromethane; at -55 - 0 ℃; Inert atmosphere; Molecular sieve;

DOI:10.1021/jo101779v

Reference yield:

phenyl 2-azido-3-O-benzyl-2-deoxy-1-thio-β-D-mannopyranoside (1256814-96-6) → 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 (1185882-49-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane; water

2.1: potassium carbonate / N,N-dimethyl-formamide / 0.75 h

3.1: pyridine / 3 h / 20 °C

4.1: tri-tert-butyl phosphine; trifluoromethylsulfonic anhydride; 1,1'-sulfinylbisbenzene / dichloromethane / 0.25 h / -65 - 55 °C / Inert atmosphere; Molecular sieve

4.2: -55 - 0 °C / Inert atmosphere; Molecular sieve

With pyridine; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tri-tert-butyl phosphine; trifluoromethylsulfonic anhydride; [bis(acetoxy)iodo]benzene; 1,1'-sulfinylbisbenzene; potassium carbonate; In dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jo101779v

upstream raw materials:

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

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

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

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