2,5-di-O-benzyl-3-deoxy-3-N-methylacetamido-β-D-xylofuranosyl chloride

Base Information

• Chemical Name: 2,5-di-O-benzyl-3-deoxy-3-N-methylacetamido-β-D-xylofuranosyl chloride
• CAS No.: 79249-16-4
• Molecular Formula: C₂₂H₂₆ClNO₄
• Molecular Weight: 403.906
• Mol file: 79249-16-4.mol

Synonyms:

Chemical Property of 2,5-di-O-benzyl-3-deoxy-3-N-methylacetamido-β-D-xylofuranosyl chloride

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,5-di-O-benzyl-3-deoxy-3-N-methylacetamido-β-D-xylofuranosyl chloride

There total 1 articles about 2,5-di-O-benzyl-3-deoxy-3-N-methylacetamido-β-D-xylofuranosyl chloride 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:

1-O-acetyl-2,5-di-O-benzyl-3-deoxy-3-N-methylacetamido-D-xylofuranose (79249-13-1,79249-14-2) → 2,5-di-O-benzyl-3-deoxy-3-N-methylacetamido-β-D-xylofuranosyl chloride (79249-16-4) + 2,5-di-O-benzyl-3-deoxy-3-N-methylacetamido-α-D-xylofuranosyl chloride (79249-15-3)

Guidance literature:

With hydrogenchloride; acetyl chloride; In 1,4-dioxane; at 25 ℃; for 5.5h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1039/P19810002151

Reference yield: 10.0%

1,3,2',6'-tetrakis-N-benzyloxycarbonylgentamine C1 (50908-08-2) + 2,5-di-O-benzyl-3-deoxy-3-N-methylacetamido-D-xylofuranosyl chloride (79249-15-3,79249-16-4) → O-3-deoxy-3-methylamino-α-D-xylofuranosyl-(1->6)-gentamine C1 (79249-19-7) + O-3-deoxy-3-methylamino-α-D-xylofuranosyl-(1->5)-gentamine C1 (79249-21-1)

Guidance literature:

With sodium hydroxide; ammonia; silver(I) 4-methylbenzenesulfonate; sodium; Yield given. Multistep reaction; 1.) dichloromethane, 25 deg C, 115 h, 2.) tetrahydrofuran, -79 deg C, 0.5 h, 3.) reflux, 6 h;

DOI:10.1039/P19810002151

Reference yield:

1,3,2',6'-tetrakis-N-benzyloxycarbonylgentamine C1 (50908-08-2) + 2,5-di-O-benzyl-3-deoxy-3-N-methylacetamido-D-xylofuranosyl chloride (79249-15-3,79249-16-4) → O-2,5-di-O-benzyl-3-deoxy-3-N-methylacetamido-α-D-xylofuranosyl-(1->5)-1,3,2',6'-tetrakis-N-benzyloxycarbonylgentamine C1 (79249-20-0) + O-2,5-di-O-benzyl-3-deoxy-3-N-methylacetamido-α-D-xylofuranosyl-(1->6)-1,3,2',6'-tetrakis-N-benzyloxycarbonylgentamine C1 (79249-18-6)

Guidance literature:

With silver(I) 4-methylbenzenesulfonate; In dichloromethane; at 25 ℃; for 115h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1039/P19810002151

upstream raw materials:

1-O-acetyl-2,5-di-O-benzyl-3-deoxy-3-N-methylacetamido-D-xylofuranose

Downstream raw materials:

O-3-deoxy-3-methylamino-α-D-xylofuranosyl-(1->6)-gentamine C₁

O-3-deoxy-3-methylamino-α-D-xylofuranosyl-(1->5)-gentamine C₁

O-2,5-di-O-benzyl-3-deoxy-3-N-methylacetamido-α-D-xylofuranosyl-(1->5)-1,3,2',6'-tetrakis-N-benzyloxycarbonylgentamine C₁

O-2,5-di-O-benzyl-3-deoxy-3-N-methylacetamido-α-D-xylofuranosyl-(1->6)-1,3,2',6'-tetrakis-N-benzyloxycarbonylgentamine C₁