1-O-(2'-acetoxy)benzoyl-3,4,6-tri-O-benzyl-α-D-2-deoxyglucopyranose

Base Information

• Chemical Name: 1-O-(2'-acetoxy)benzoyl-3,4,6-tri-O-benzyl-α-D-2-deoxyglucopyranose
• CAS No.: 74545-16-7
• Molecular Formula: C₃₆H₃₆O₈
• Molecular Weight: 596.677
• Mol file: 74545-16-7.mol

Synonyms:1-O-(2'-acetoxy)benzoyl-3,4,6-tri-O-benzyl-α-D-2-deoxyglucopyranose

Chemical Property of 1-O-(2'-acetoxy)benzoyl-3,4,6-tri-O-benzyl-α-D-2-deoxyglucopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-O-(2'-acetoxy)benzoyl-3,4,6-tri-O-benzyl-α-D-2-deoxyglucopyranose

There total 4 articles about 1-O-(2'-acetoxy)benzoyl-3,4,6-tri-O-benzyl-α-D-2-deoxyglucopyranose 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: 25.0%

3,4,6-Tri-O-benzyl-2-deoxy-α-D-arabino-hexopyranose (74545-15-6) + O-acetylsalicyloyl chloride (5538-51-2) → 1-O-(2'-acetoxy)benzoyl-3,4,6-tri-O-benzyl-α-D-2-deoxyglucopyranose (74545-16-7)

Guidance literature:

With pyridine; In dichloromethane; at 20 ℃; for 23h;

DOI:10.1002/jps.2600690237

Reference yield:

D-2-deoxyglucose (154-17-6) → 1-O-(2'-acetoxy)benzoyl-3,4,6-tri-O-benzyl-α-D-2-deoxyglucopyranose (74545-16-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 61 percent / HCl / 1 h / 40 °C

2: 1.) KOH / 1) reflux, dioxane; 2) dioxane, reflux, 4 h 25 min

3: 65 percent / aq. H₂SO₄ / acetic acid / 1) 70 deg C, 1 h; 2) 10 deg C, 26 h

4: 25 percent / pyridine / CH₂Cl₂ / 23 h / 20 °C

With pyridine; hydrogenchloride; potassium hydroxide; sulfuric acid; In dichloromethane; acetic acid;

DOI:10.1002/jps.2600690237

Reference yield:

methyl 2-deoxy-3,4,6-tris-O-(phenylmethyl)-α-D-arabino-hexopyranoside (74545-14-5) → 1-O-(2'-acetoxy)benzoyl-3,4,6-tri-O-benzyl-α-D-2-deoxyglucopyranose (74545-16-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 65 percent / aq. H₂SO₄ / acetic acid / 1) 70 deg C, 1 h; 2) 10 deg C, 26 h

2: 25 percent / pyridine / CH₂Cl₂ / 23 h / 20 °C

With pyridine; sulfuric acid; In dichloromethane; acetic acid;

DOI:10.1002/jps.2600690237

upstream raw materials:

3,4,6-Tri-O-benzyl-2-deoxy-α-D-arabino-hexopyranose

O-acetylsalicyloyl chloride

D-2-deoxyglucose

methyl 2-deoxy-3,4,6-tris-O-(phenylmethyl)-α-D-arabino-hexopyranoside

Downstream raw materials:

1-O-(2'-acetoxy)benzoyl-α-D-2-deoxyglucopyranose