1,6-di-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranose

Base Information

• Chemical Name: 1,6-di-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranose
• CAS No.: 55682-49-0
• Molecular Formula: C₂₄H₂₇N₃O₇
• Molecular Weight: 469.494
• Mol file: 55682-49-0.mol

Synonyms:1,6-di-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranose

Chemical Property of 1,6-di-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranose

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

1,6-Di-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-alpha-D-glucopyranose 99%min ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,6-di-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranose

There total 9 articles about 1,6-di-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranose 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:

acetic anhydride (108-24-7) + 1,6-anhydro-2-azido-3,4-di-O-benzyl-2-deoxy-D-glucopyranose (55682-48-9) → 1,6-di-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranose (55682-49-0)

Guidance literature:

With trifluoroacetic acid; at 20 ℃; Inert atmosphere;

Reference yield:

acetic anhydride (108-24-7) + 1,6-anhydro-2-azido-3,4-di-O-benzyl-2-deoxy-D-glucopyranose (55682-48-9) → 1,6-di-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranose (55682-49-0) + 1,6-di-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranose (133076-39-8)

Guidance literature:

With trifluoroacetic acid; at 20 ℃;

Reference yield:

α-D-glucopyranose peracetylate (604-68-2) → 1,6-di-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranose (55682-49-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: hydrogen bromide; acetic acid / 2 h / 20 °C / Industry scale

1.2: 2 h / 0 - 5 °C / Industry scale

2.1: sodium methylate / methanol / 5 - 20 °C / pH 9 - 9.5 / Industry scale

2.2: 5 h / Reflux; Molecular sieve; Industry scale

2.3: 0 - 20 °C

3.1: sodium hydrogencarbonate / N,N-dimethyl-formamide / 20 - 122 °C / Industry scale

4.1: potassium hydroxide / tetrabutylammomium bromide / toluene; 1-methyl-pyrrolidin-2-one / 0 - 20 °C / Industry scale

5.1: trifluoroacetic acid / 20 °C / Inert atmosphere

With hydrogen bromide; sodium methylate; sodium hydrogencarbonate; acetic acid; trifluoroacetic acid; potassium hydroxide; tetrabutylammomium bromide; In 1-methyl-pyrrolidin-2-one; methanol; N,N-dimethyl-formamide; toluene;

upstream raw materials:

acetic anhydride

1,6-anhydro-2-azido-3,4-di-O-benzyl-2-deoxy-D-glucopyranose

α-D-glucopyranose peracetylate

alpha-D-glucopyranose

Downstream raw materials:

3-O-(2-Acetamido-6-O-acetyl-3,4-di-O-benzyl-2-desoxy-α-D-glucopyranosyl)-1,6-anhydro-2,4-di-O-benzyl-β-D-galactopyranose

3-O-(2-Acetamido-6-O-acetyl-3,4-di-O-benzyl-2-desoxy-α-D-glucopyranosyl)-1,6-di-O-acetyl-2,4-di-O-benzyl-β-D-galactopyranose

3-O-(2-Acetamido-6-O-acetyl-3,4-di-O-benzyl-2-desoxy-α-D-glucopyranosyl)-1,6-di-O-acetyl-2,4-di-O-benzyl-α-D-galactopyranose

6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl bromide