methyl 1-O-acetyl-2,3-di-O-benzoyl-4-O-p-methoxybenzyl-β-D-glucuronate

Base Information

• Chemical Name: methyl 1-O-acetyl-2,3-di-O-benzoyl-4-O-p-methoxybenzyl-β-D-glucuronate
• CAS No.: 1287768-31-3
• Molecular Formula: C₃₁H₃₀O₁₁
• Molecular Weight: 578.573
• Mol file: 1287768-31-3.mol

Synonyms:methyl 1-O-acetyl-2,3-di-O-benzoyl-4-O-p-methoxybenzyl-β-D-glucuronate

Chemical Property of methyl 1-O-acetyl-2,3-di-O-benzoyl-4-O-p-methoxybenzyl-β-D-glucuronate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 1-O-acetyl-2,3-di-O-benzoyl-4-O-p-methoxybenzyl-β-D-glucuronate

There total 8 articles about methyl 1-O-acetyl-2,3-di-O-benzoyl-4-O-p-methoxybenzyl-β-D-glucuronate 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: 61.0%

methyl phenyl 2,3-di-O-benzoyl-4-O-p-methoxybenzyl-1-thio-β-D-glucuronate (1287768-30-2) + acetic anhydride (108-24-7) → methyl 1-O-acetyl-2,3-di-O-benzoyl-4-O-p-methoxybenzyl-β-D-glucuronate (1287768-31-3) + methyl 1-O-acetyl-2,3-di-O-benzoyl-4-O-p-methoxybenzyl-α-D-glucuronate

Guidance literature:

methyl phenyl 2,3-di-O-benzoyl-4-O-p-methoxybenzyl-1-thio-β-D-glucuronate; With N-iodo-succinimide; acetic acid; In dichloromethane; at 20 ℃;

acetic anhydride; With pyridine; optical yield given as %de;

DOI:10.1021/jo200076z

Reference yield:

phenyl 2,3-di-O-benzoyl-4,6-O-p-methoxy-benzylidene-1-thio-β-D-glucopyranoside (1287768-28-8) → methyl 1-O-acetyl-2,3-di-O-benzoyl-4-O-p-methoxybenzyl-β-D-glucuronate (1287768-31-3) + methyl 1-O-acetyl-2,3-di-O-benzoyl-4-O-p-methoxybenzyl-α-D-glucuronate

Guidance literature:

Multi-step reaction with 4 steps

1.1: triethylsilane; phenylborondichloride / dichloromethane / 0.5 h / -78 °C / Molecular sieve; Inert atmosphere

2.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane; water / 20 °C

3.1: caesium carbonate / N,N-dimethyl-formamide / 0 °C

3.2: 1 h / 0 °C

4.1: N-iodo-succinimide; acetic acid / dichloromethane / 20 °C

With triethylsilane; N-iodo-succinimide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; phenylborondichloride; caesium carbonate; acetic acid; In dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jo200076z

Reference yield:

phenyl 2,3-di-O-benzoyl-4-O-p-methoxybenzyl-1-thio-β-D-glucopyranoside (1287768-29-9) → methyl 1-O-acetyl-2,3-di-O-benzoyl-4-O-p-methoxybenzyl-β-D-glucuronate (1287768-31-3) + methyl 1-O-acetyl-2,3-di-O-benzoyl-4-O-p-methoxybenzyl-α-D-glucuronate

Guidance literature:

Multi-step reaction with 3 steps

1.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane; water / 20 °C

2.1: caesium carbonate / N,N-dimethyl-formamide / 0 °C

2.2: 1 h / 0 °C

3.1: N-iodo-succinimide; acetic acid / dichloromethane / 20 °C

With N-iodo-succinimide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; caesium carbonate; acetic acid; In dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jo200076z

upstream raw materials:

phenyl 2,3-di-O-benzoyl-4,6-O-p-methoxy-benzylidene-1-thio-β-D-glucopyranoside

phenyl 2,3-di-O-benzoyl-4-O-p-methoxybenzyl-1-thio-β-D-glucopyranoside

C₃₄H₃₀O₉S

methyl phenyl 2,3-di-O-benzoyl-4-O-p-methoxybenzyl-1-thio-β-D-glucuronate

Downstream raw materials:

methyl 2,3-di-O-benzoyl-1-azido-β-D-glucuronate

C₅₃H₅₄N₄O₁₄

C₄₃H₄₆N₄O₁₆

C₅₆H₅₆N₄O₁₄