28-O-benzyl-3-O-[2-acetamido-3,4-O-bi-acetyl-6-O-2-deoxy-β-D-glucopyranosyl]oleanolic ester

Base Information

• Chemical Name: 28-O-benzyl-3-O-[2-acetamido-3,4-O-bi-acetyl-6-O-2-deoxy-β-D-glucopyranosyl]oleanolic ester
• CAS No.: 1616703-81-1
• Molecular Formula: C₄₉H₇₁NO₁₀
• Molecular Weight: 834.103
• Mol file: 1616703-81-1.mol

Synonyms:28-O-benzyl-3-O-[2-acetamido-3,4-O-bi-acetyl-6-O-2-deoxy-β-D-glucopyranosyl]oleanolic ester

Chemical Property of 28-O-benzyl-3-O-[2-acetamido-3,4-O-bi-acetyl-6-O-2-deoxy-β-D-glucopyranosyl]oleanolic ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 28-O-benzyl-3-O-[2-acetamido-3,4-O-bi-acetyl-6-O-2-deoxy-β-D-glucopyranosyl]oleanolic ester

There total 5 articles about 28-O-benzyl-3-O-[2-acetamido-3,4-O-bi-acetyl-6-O-2-deoxy-β-D-glucopyranosyl]oleanolic ester 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: 71.2%

28-O-benzyl-3-O-[3,4-O-bi-acetyl-6-O-tert-butyldimethylsilyl-2-acetamido-2-deoxy-β-D-glucopyranosyl]oleanolic ester (1616703-80-0) → 28-O-benzyl-3-O-[2-acetamido-3,4-O-bi-acetyl-6-O-2-deoxy-β-D-glucopyranosyl]oleanolic ester (1616703-81-1)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 11h;

DOI:10.1039/c4ob00874j

Reference yield:

Oleanolic acid (508-02-1) → 28-O-benzyl-3-O-[2-acetamido-3,4-O-bi-acetyl-6-O-2-deoxy-β-D-glucopyranosyl]oleanolic ester (1616703-81-1)

Guidance literature:

Multi-step reaction with 8 steps

1.1: tetrabutyl ammonium fluoride; sodium hydrogencarbonate / dichloromethane

2.1: dichloromethane / 0.5 h / 20 °C

2.2: 3 h / 0 °C

3.1: acetic acid; zinc / 4 h

4.1: pyridine / 1.5 h

5.1: sodium methylate / dichloromethane; methanol / pH 7

6.1: 1H-imidazole / dichloromethane / 0.17 h

7.1: pyridine / 2.5 h

8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 11 h

With pyridine; 1H-imidazole; tetrabutyl ammonium fluoride; sodium methylate; sodium hydrogencarbonate; acetic acid; zinc; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1039/c4ob00874j

Reference yield:

benzyl bromide (100-39-0) → 28-O-benzyl-3-O-[2-acetamido-3,4-O-bi-acetyl-6-O-2-deoxy-β-D-glucopyranosyl]oleanolic ester (1616703-81-1)

Guidance literature:

Multi-step reaction with 8 steps

1.1: tetrabutyl ammonium fluoride; sodium hydrogencarbonate / dichloromethane

2.1: dichloromethane / 0.5 h / 20 °C

2.2: 3 h / 0 °C

3.1: acetic acid; zinc / 4 h

4.1: pyridine / 1.5 h

5.1: sodium methylate / dichloromethane; methanol / pH 7

6.1: 1H-imidazole / dichloromethane / 0.17 h

7.1: pyridine / 2.5 h

8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 11 h

With pyridine; 1H-imidazole; tetrabutyl ammonium fluoride; sodium methylate; sodium hydrogencarbonate; acetic acid; zinc; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1039/c4ob00874j

upstream raw materials:

Oleanolic acid

benzyl bromide

oleanolic acid benzyl ester

28-O-benzyl-3-O-[3′,4′,6′-tri-O-acetyl-2′-deoxy-2′-(2″,2″,2″-trichloroethyloxycarbonylamino)-β-D-glucopyranosyl]oleanolic ester