2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl azide

Base Information

• Chemical Name: 2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl azide
• CAS No.: 522634-50-0
• Molecular Formula: C₂₂H₂₆N₄O₅
• Molecular Weight: 426.472
• Mol file: 522634-50-0.mol

Synonyms:2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl azide

Chemical Property of 2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl azide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl azide

There total 1 articles about 2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl azide 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%

2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl azide (80887-27-0) → 2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl azide (522634-50-0)

Guidance literature:

With hydrogenchloride; sodium cyanoborohydride; In tetrahydrofuran; diethyl ether; for 1.5h; Heating;

DOI:10.1081/CAR-120016847

Reference yield: 90.0%

succinic acid anhydride (108-30-5) + 2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl azide (522634-50-0) → 2-acetamido-3,6-di-O-benzyl-4-O-succinoyl-2-deoxy-β-D-glucopyranosyl azide (522634-51-1)

Guidance literature:

With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In dichloromethane; at 20 ℃;

DOI:10.1081/CAR-120016847

Reference yield:

2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl azide (522634-50-0) → 2-acetamido-4-O-[3-[[(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)amino]carbonyl]propanoyl]-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosylamine (522634-54-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / EDC; HOBt; NEt₃ / CH₂Cl₂ / 20 °C

2: 65 percent / molecular sieves (4 Angstroem); EDC; HOBt / NEt₃ / CH₂Cl₂ / 30 h / 20 °C

3: 93 percent / hydrogen / Pd/C / methanol / 0.58 h / 20 - 60 °C

With 4 A molecular sieve; hydrogen; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; palladium on activated charcoal; triethylamine; In methanol; dichloromethane;

DOI:10.1081/CAR-120016847

upstream raw materials:

2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl azide

Downstream raw materials:

2-acetamido-3,6-di-O-benzyl-4-O-succinoyl-2-deoxy-β-D-glucopyranosyl azide

2-acetamido-4-O-[3-[[(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)amino]carbonyl]propanoyl]-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranose

2-acetamido-4-O-[3-[[(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)amino]carbonyl]propanoyl]-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosylamine

2-acetamido-4-O-[3-[[(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)amino]carbonyl]propanoyl]-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl azide

Refernces