phenyl 2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-6-O-(p-methoxyphenyl)-1-thio-α-L-idopyranoside

Base Information

• Chemical Name: phenyl 2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-6-O-(p-methoxyphenyl)-1-thio-α-L-idopyranoside
• CAS No.: 1447801-67-3
• Molecular Formula: C₃₈H₃₈O₉S
• Molecular Weight: 670.78
• Mol file: 1447801-67-3.mol

Synonyms:phenyl 2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-6-O-(p-methoxyphenyl)-1-thio-α-L-idopyranoside

Chemical Property of phenyl 2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-6-O-(p-methoxyphenyl)-1-thio-α-L-idopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-6-O-(p-methoxyphenyl)-1-thio-α-L-idopyranoside

There total 4 articles about phenyl 2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-6-O-(p-methoxyphenyl)-1-thio-α-L-idopyranoside 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: 90.0%

phenyl 2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-6-O-(p-methoxyphenyl)-1-thio-α-L-idopyranoside (1447801-78-6) + levulinic acid (123-76-2) → phenyl 2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-6-O-(p-methoxyphenyl)-1-thio-α-L-idopyranoside (1447801-67-3)

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20 ℃; for 5h;

DOI:10.1021/jo400467g

Reference yield:

C21H22O6 → phenyl 2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-6-O-(p-methoxyphenyl)-1-thio-α-L-idopyranoside (1447801-67-3)

Guidance literature:

Multi-step reaction with 3 steps

1: zinc(II) iodide / dichloromethane / 20 °C

2: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 20 °C

3: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 5 h / 20 °C

With dmap; di-isopropyl azodicarboxylate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine; zinc(II) iodide; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo400467g

Reference yield:

phenylthiotrimethylsilane (4551-15-9) → phenyl 2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-6-O-(p-methoxyphenyl)-1-thio-α-L-idopyranoside (1447801-67-3)

Guidance literature:

Multi-step reaction with 3 steps

1: zinc(II) iodide / dichloromethane / 20 °C

2: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 20 °C

3: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 5 h / 20 °C

With dmap; di-isopropyl azodicarboxylate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine; zinc(II) iodide; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo400467g

upstream raw materials:

phenyl 2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-6-O-(p-methoxyphenyl)-1-thio-α-L-idopyranoside

levulinic acid

phenylthiotrimethylsilane

phenyl 2-O-benzoyl-3-O-benzyl-4,6-dihydroxylthio-α-L-idopyranoside

Downstream raw materials:

4-(acetoxymethyl)benzyl N-benzyl-N-[5-(2-O-acetyl-4-O-(6-O-acetyl-2-azido-4-O-(2,4-di-O-acetyl-3-O-benzyl-6-O-(p-methoxyphenyl)-α-L-idopyranosyl)-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3-O-benzyl-6-O-(p-methoxyphenyl)-α-L-idopyranosyloxy)pentyl]carbamate

N-benzyl-N-[5-((4-O-(2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3-O-benzyl-6-O-(p-methoxyphenyl)-α-L-idopyranosyl)oxy)pentyl]carbamate

4-(phenylcarboxymethyl)benzyl N-benzyl N-(5-(2-O-benzoyl-3-O-benzyl-6-O-para-methoxyphenyl-α-L-idopyranosyloxy)pentyl)carbamate

4-(phenylcarboxymethyl)benzyl N-benzyl N-(5-(2-O-benzoyl-3-O-benzyl-6-O-para-methoxybenzyl-α-L-idopyranosyloxy)pentyl)carbamate