2,3,4-Tri-O-acetyl-β-L-rhamnopyranosyl azide

Base Information

• Chemical Name: 2,3,4-Tri-O-acetyl-β-L-rhamnopyranosyl azide
• CAS No.: 95580-98-6
• Molecular Formula: C₁₂H₁₇N₃O₇
• Molecular Weight: 315.283
• Mol file: 95580-98-6.mol

Synonyms:

Chemical Property of 2,3,4-Tri-O-acetyl-β-L-rhamnopyranosyl azide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,3,4-Tri-O-acetyl-β-L-rhamnopyranosyl azide

There total 2 articles about 2,3,4-Tri-O-acetyl-β-L-rhamnopyranosyl 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:

2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl bromide (5158-64-5) → 2,3,4-tri-O-acetyl-6-deoxy-α-L-mannopyranosyl azide (95580-90-8) + 2,3,4-Tri-O-acetyl-β-L-rhamnopyranosyl azide (95580-98-6)

Guidance literature:

With sodium azide; In N,N,N,N,N,N-hexamethylphosphoric triamide; at 75 ℃; for 0.833333h;

DOI:10.1002/jlac.198519850112

Reference yield:

1,2,3,4-tetra-O-acetyl-L-rhamnopyranose (7404-35-5,17081-04-8,20853-37-6,24332-95-4,27821-10-9,27821-11-0,33947-15-8,34371-40-9,34371-41-0,35521-79-0,36807-81-5,36807-82-6,50615-78-6,51921-33-6,62182-03-0,64913-16-2,70004-81-8,84622-47-9,87303-56-8,108942-32-1,108942-33-2,109430-94-6,143394-72-3,30021-94-4) → 2,3,4-tri-O-acetyl-6-deoxy-α-L-mannopyranosyl azide (95580-90-8) + 2,3,4-Tri-O-acetyl-β-L-rhamnopyranosyl azide (95580-98-6)

Guidance literature:

With trimethylsilylazide; tin(IV) chloride; In dichloromethane; for 1h; Title compound not separated from byproducts; Ambient temperature;

Reference yield:

2,3,4-Tri-O-acetyl-β-L-rhamnopyranosyl azide (95580-98-6) → 4-aminosulfonyl-N-(β-L-rhamnosyl)benzamide

Guidance literature:

Multi-step reaction with 3 steps

1: palladium on activated charcoal; hydrogen / ethyl acetate / 2 h

2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 2 h / 20 °C

3: sodium methylate; methanol / dichloromethane / 20 °C

With methanol; palladium on activated charcoal; hydrogen; sodium methylate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; ethyl acetate;

DOI:10.1080/14756366.2019.1705293

upstream raw materials:

1,2,3,4-tetra-O-acetyl-L-rhamnopyranose

2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl bromide