2-Acetamido-1,6-anhydro-4-O-benzyl-3,O-<(1R)-1-carboxyethyl>-2-desoxy-β-D-glucopyranose

Base Information

• Chemical Name: 2-Acetamido-1,6-anhydro-4-O-benzyl-3,O-<(1R)-1-carboxyethyl>-2-desoxy-β-D-glucopyranose
• CAS No.: 104430-65-1
• Molecular Formula: C₁₈H₂₃NO₇
• Molecular Weight: 365.383
• Mol file: 104430-65-1.mol

Synonyms:2-Acetamido-1,6-anhydro-4-O-benzyl-3,O-<(1R)-1-carboxyethyl>-2-desoxy-β-D-glucopyranose

Chemical Property of 2-Acetamido-1,6-anhydro-4-O-benzyl-3,O-<(1R)-1-carboxyethyl>-2-desoxy-β-D-glucopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-Acetamido-1,6-anhydro-4-O-benzyl-3,O-<(1R)-1-carboxyethyl>-2-desoxy-β-D-glucopyranose

There total 6 articles about 2-Acetamido-1,6-anhydro-4-O-benzyl-3,O-<(1R)-1-carboxyethyl>-2-desoxy-β-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: 44.0%

2-acetylamino-1,6-anhydro-2-deoxy-4-O-benzyl-3-O-[(1R)-1-(ethyoxycarbonyl)ethyl]-β-D-glucopyranose (1104583-56-3) → 2-Acetamido-1,6-anhydro-4-O-benzyl-3,O-<(1R)-1-carboxyethyl>-2-desoxy-β-D-glucopyranose (104430-65-1)

Guidance literature:

With lithium hydroxide monohydrate; water; In tetrahydrofuran; 1,4-dioxane; for 1.5h;

DOI:10.1002/chem.200801121

Reference yield:

2-amino-1,6-anhydro-4-O-benzyl-2-deoxy-3-O-[(1R)-1-carboxyethyl]-β-D-glucopyranose + acetic anhydride (108-24-7) → 2-Acetamido-1,6-anhydro-4-O-benzyl-3,O-<(1R)-1-carboxyethyl>-2-desoxy-β-D-glucopyranose (104430-65-1)

Guidance literature:

In dichloromethane; at 20 ℃; for 20h; Inert atmosphere;

Reference yield:

(R)-2-(((1R,2S,3R,4R,5R)-4-azido-2-(benzyloxy)-6,8-dioxabicyclo[3.2.1]octan-3-yl)oxy)propanoic acid (104430-61-7) → 2-Acetamido-1,6-anhydro-4-O-benzyl-3,O-<(1R)-1-carboxyethyl>-2-desoxy-β-D-glucopyranose (104430-65-1)

Guidance literature:

Multi-step reaction with 3 steps

1: methanol; diethyl ether / 1 h

2: 82 percent / H₂ / 10percent Pd/C / dioxane / 1.5 h / 26252.1 Torr / Ambient temperature

3: 950 mg / 1N KOH (aq) / dioxane; methanol / 0.5 h

With potassium hydroxide; hydrogen; palladium on activated charcoal; In 1,4-dioxane; methanol; diethyl ether;

DOI:10.1002/jlac.198619860408

upstream raw materials:

2-Acetamido-1,6-anhydro-4-O-benzyl-2-desoxy-3-O-<(1R)-1-(methoxycarbonyl)ethyl>-β-D-glucopyranose

(R)-2-(((1R,2S,3R,4R,5R)-4-azido-2-(benzyloxy)-6,8-dioxabicyclo[3.2.1]octan-3-yl)oxy)propanoic acid

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

1,6-Anhydro-2-azido-4-O-benzyl-2-desoxy-3-O-<(1R)-1-(methoxycarbonyl)ethyl>-β-D-glucopyranose

Downstream raw materials:

2-Acetamido-1,6-anhydro-4-O-benzyl-β-muramoyl-L-alanyl-D-isoglutamin-benzylester

2-acetamido-1,6-anhydro-4-O-benzyl-2-deoxy-3-O-{[(2R)-N-phenylpropionamide]-2-yl}-β-D-glucopyranose