p-tolyl 4-O-acetyl-3-O-(p-methoxybenzyl)-2-O-levulinoyl-1-thio-α-L-rhamnopyranoside

Base Information

• Chemical Name: p-tolyl 4-O-acetyl-3-O-(p-methoxybenzyl)-2-O-levulinoyl-1-thio-α-L-rhamnopyranoside
• CAS No.: 943221-78-1
• Molecular Formula: C₂₈H₃₄O₈S
• Molecular Weight: 530.639
• Mol file: 943221-78-1.mol

Synonyms:p-tolyl 4-O-acetyl-3-O-(p-methoxybenzyl)-2-O-levulinoyl-1-thio-α-L-rhamnopyranoside

Chemical Property of p-tolyl 4-O-acetyl-3-O-(p-methoxybenzyl)-2-O-levulinoyl-1-thio-α-L-rhamnopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of p-tolyl 4-O-acetyl-3-O-(p-methoxybenzyl)-2-O-levulinoyl-1-thio-α-L-rhamnopyranoside

There total 4 articles about p-tolyl 4-O-acetyl-3-O-(p-methoxybenzyl)-2-O-levulinoyl-1-thio-α-L-rhamnopyranoside 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: 56.9%

4-O-acetyl-3-O-(4-methoxy)benzyl-1-(4-tolyl)thio-α-L-rhamnopyranoside (943221-86-1) + levulinic acid (123-76-2) → p-tolyl 4-O-acetyl-3-O-(p-methoxybenzyl)-2-O-levulinoyl-1-thio-α-L-rhamnopyranoside (943221-78-1)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane;

DOI:10.1016/j.carres.2007.03.014

Reference yield:

p-tolyl 4-O-acetyl-2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside (851625-43-9) → p-tolyl 4-O-acetyl-3-O-(p-methoxybenzyl)-2-O-levulinoyl-1-thio-α-L-rhamnopyranoside (943221-78-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 93.1 percent / AcOH; water / 1.5 h / 80 °C

2.1: Bu₂SnO / toluene / 6 h / Heating

2.2: 74.1 percent / Bu₄NI / dimethylformamide / 36 h / 20 °C

3.1: 56.9 percent / N,N'-dicyclohexylcarbodiimide; 4-N,N-dimethylaminopyridine / CH₂Cl₂

With dmap; water; di(n-butyl)tin oxide; acetic acid; dicyclohexyl-carbodiimide; In dichloromethane; toluene;

DOI:10.1016/j.carres.2007.03.014

Reference yield:

p-tolyl 4-O-acetyl-1-thio-α-L-rhamnopyranoside (943221-81-6) → p-tolyl 4-O-acetyl-3-O-(p-methoxybenzyl)-2-O-levulinoyl-1-thio-α-L-rhamnopyranoside (943221-78-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Bu₂SnO / toluene / 6 h / Heating

1.2: 74.1 percent / Bu₄NI / dimethylformamide / 36 h / 20 °C

2.1: 56.9 percent / N,N'-dicyclohexylcarbodiimide; 4-N,N-dimethylaminopyridine / CH₂Cl₂

With dmap; di(n-butyl)tin oxide; dicyclohexyl-carbodiimide; In dichloromethane; toluene;

DOI:10.1016/j.carres.2007.03.014

upstream raw materials:

4-O-acetyl-3-O-(4-methoxy)benzyl-1-(4-tolyl)thio-α-L-rhamnopyranoside

levulinic acid

p-tolyl 4-O-acetyl-2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside

p-tolyl 4-O-acetyl-1-thio-α-L-rhamnopyranoside

Downstream raw materials:

dodecanyl 4-O-acetyl-3-O-(p-methoxybenzyl)-2-O-levulinoyl-α-L-rhamnopyranosyl-(1->4)-2,3-O-isopropylidene-α-L-rhamnopyranoside

p-tolyl 4-O-acetyl-2-O-levulinyl-1-thio-α-L-rhamnopyranoside

p-tolyl 4-O-acetyl-2,3-O-isopropylidene-α-L-rhamnopyranosyl-(1->3)-4-O-acetyl-2-O-levulinyl-1-thio-α-L-rhamnopyranoside