allyl 2-acetamido-2-deoxy-3-O-levulinoyl-4,6-O-p-methoxybenzylidene-β-D-glucopyranoside

Base Information

• Chemical Name: allyl 2-acetamido-2-deoxy-3-O-levulinoyl-4,6-O-p-methoxybenzylidene-β-D-glucopyranoside
• CAS No.: 1314876-68-0
• Molecular Formula: C₂₄H₃₁NO₉
• Molecular Weight: 477.511
• Mol file: 1314876-68-0.mol

Synonyms:allyl 2-acetamido-2-deoxy-3-O-levulinoyl-4,6-O-p-methoxybenzylidene-β-D-glucopyranoside

Chemical Property of allyl 2-acetamido-2-deoxy-3-O-levulinoyl-4,6-O-p-methoxybenzylidene-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of allyl 2-acetamido-2-deoxy-3-O-levulinoyl-4,6-O-p-methoxybenzylidene-β-D-glucopyranoside

There total 2 articles about allyl 2-acetamido-2-deoxy-3-O-levulinoyl-4,6-O-p-methoxybenzylidene-β-D-glucopyranoside 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: 74.0%

allyl 2-acetamido-2-deoxy-4,6-O-p-methoxybenzylidene-β-D-glucopyranoside (131204-03-0,136520-23-5,136983-80-7) + levulinic acid (123-76-2) → allyl 2-acetamido-2-deoxy-3-O-levulinoyl-4,6-O-p-methoxybenzylidene-β-D-glucopyranoside (1314876-68-0)

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20 ℃;

DOI:10.2174/157017811795685090

Reference yield:

allyl 2-acetamido-2-deoxy-β-D-glucopyranoside (54400-75-8,64650-83-5,88903-97-3,116347-86-5,140849-88-3,144300-01-6,54400-77-0) → allyl 2-acetamido-2-deoxy-3-O-levulinoyl-4,6-O-p-methoxybenzylidene-β-D-glucopyranoside (1314876-68-0)

Guidance literature:

Multi-step reaction with 2 steps

1: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 24 h / 20 °C

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

With dmap; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.2174/157017811795685090

Reference yield:

allyl 2-acetamido-2-deoxy-3-O-levulinoyl-4,6-O-p-methoxybenzylidene-β-D-glucopyranoside (1314876-68-0) → α-D-mannopyranosyl-(1->3)-2-amino-1,2-deoxy-1-(2-triphenylmethylthioeth-2-ylamino)-D-glucitol (1314876-73-7)

Guidance literature:

Multi-step reaction with 7 steps

1: tetrafluoroboric acid / methanol; dichloromethane / 2 h / 20 °C

2: pyridine / 10 h / 20 °C

3: hydrazinium monoacetate / ethanol; toluene / 20 °C

4: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 7 h / -30 - 20 °C / Molecular sieve; Inert atmosphere

5: methanol; palladium dichloride / dichloromethane / 7 h / 20 °C

6: methanol; sodium methylate / dichloromethane / 4 h / 20 °C

7: sodium cyanoborohydride; acetic acid / dimethyl sulfoxide / 4 h / 65 °C / Inert atmosphere

With pyridine; methanol; tetrafluoroboric acid; trimethylsilyl trifluoromethanesulfonate; sodium methylate; hydrazinium monoacetate; sodium cyanoborohydride; acetic acid; palladium dichloride; In methanol; ethanol; dichloromethane; dimethyl sulfoxide; toluene; 6: Zemplen deacetylation;

DOI:10.2174/157017811795685090

upstream raw materials:

allyl 2-acetamido-2-deoxy-β-D-glucopyranoside

allyl 2-acetamido-2-deoxy-4,6-O-p-methoxybenzylidene-β-D-glucopyranoside

levulinic acid

Downstream raw materials:

α-D-mannopyranosyl-(1->3)-2-amino-1,2-deoxy-1-(2-triphenylmethylthioeth-2-ylamino)-D-glucitol