methyl 4-azido-2,3-di-O-benzyl-4-deoxy-6-O-propionyl-β-D-glucopyranoside

Base Information

• Chemical Name: methyl 4-azido-2,3-di-O-benzyl-4-deoxy-6-O-propionyl-β-D-glucopyranoside
• CAS No.: 122079-62-3
• Molecular Formula: C₂₄H₂₉N₃O₆
• Molecular Weight: 455.511
• Mol file: 122079-62-3.mol

Synonyms:methyl 4-azido-2,3-di-O-benzyl-4-deoxy-6-O-propionyl-β-D-glucopyranoside

Chemical Property of methyl 4-azido-2,3-di-O-benzyl-4-deoxy-6-O-propionyl-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 4-azido-2,3-di-O-benzyl-4-deoxy-6-O-propionyl-β-D-glucopyranoside

There total 7 articles about methyl 4-azido-2,3-di-O-benzyl-4-deoxy-6-O-propionyl-β-D-glucopyranoside 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: 84.0%

methyl 2,3-di-O-benzyl-4-O-methanesulfonyl-6-O-propionyl-β-D-galactopyranoside (122079-61-2) → methyl 4-azido-2,3-di-O-benzyl-4-deoxy-6-O-propionyl-β-D-glucopyranoside (122079-62-3)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 120 - 125 ℃; for 2h;

DOI:10.1016/0008-6215(89)84037-6

Reference yield:

methyl 4,6-O-isopropylidene-β-D-galacytopyranoside (20688-90-8) → methyl 4-azido-2,3-di-O-benzyl-4-deoxy-6-O-propionyl-β-D-glucopyranoside (122079-62-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 75.5 percent / KOH / dimethylformamide / 2 h / 30 - 35 °C

2: 92.3 percent / 75percent CH₃COOH / 0.5 h / 100 °C

3: 74 percent / pyridine / 5 deg C, then room t.

4: 96.3 percent / pyridine / 4 h / 30 - 32 °C

5: 84 percent / NaN₃ / dimethylformamide / 2 h / 120 - 125 °C

With pyridine; potassium hydroxide; sodium azide; acetic acid; In N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(89)84037-6

Reference yield:

benzyl chloride (100-44-7) → methyl 4-azido-2,3-di-O-benzyl-4-deoxy-6-O-propionyl-β-D-glucopyranoside (122079-62-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 75.5 percent / KOH / dimethylformamide / 2 h / 30 - 35 °C

2: 92.3 percent / 75percent CH₃COOH / 0.5 h / 100 °C

3: 74 percent / pyridine / 5 deg C, then room t.

4: 96.3 percent / pyridine / 4 h / 30 - 32 °C

5: 84 percent / NaN₃ / dimethylformamide / 2 h / 120 - 125 °C

With pyridine; potassium hydroxide; sodium azide; acetic acid; In N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(89)84037-6

upstream raw materials:

methyl 2,3-di-O-benzyl-4-O-methanesulfonyl-6-O-propionyl-β-D-galactopyranoside

methyl 4,6-O-isopropylidene-β-D-galacytopyranoside

benzyl chloride

methyl 2,3-di-O-benzyl-6-O-propionyl-β-D-galactopyranoside

Downstream raw materials:

2,5-diazido-3-O-(4-azido-2,3-di-O-benzyl-4-deoxy-α-D-glucopyranosyl)-2,5-dideoxy-L-iditol

2,5-diazido-3-O-(4-azido-2,3-di-O-benzyl-6-O-propionyl-α-D-glucopyranosyl)-1,6-di-O-benzoyl-2,5-dideoxy-L-iditol