benzyl 2,3-di-O-acetyl-4-O-(3',4'-dinitrophenyl)-6-O-para-methoxybenzyl-β-D-glucopyranoside

Base Information

• Chemical Name: benzyl 2,3-di-O-acetyl-4-O-(3',4'-dinitrophenyl)-6-O-para-methoxybenzyl-β-D-glucopyranoside
• CAS No.: 461026-49-3
• Molecular Formula: C₃₁H₃₂N₂O₁₃
• Molecular Weight: 640.601
• Mol file: 461026-49-3.mol

Synonyms:benzyl 2,3-di-O-acetyl-4-O-(3',4'-dinitrophenyl)-6-O-para-methoxybenzyl-β-D-glucopyranoside

Chemical Property of benzyl 2,3-di-O-acetyl-4-O-(3',4'-dinitrophenyl)-6-O-para-methoxybenzyl-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 2,3-di-O-acetyl-4-O-(3',4'-dinitrophenyl)-6-O-para-methoxybenzyl-β-D-glucopyranoside

There total 9 articles about benzyl 2,3-di-O-acetyl-4-O-(3',4'-dinitrophenyl)-6-O-para-methoxybenzyl-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: 38.0%

3,4-dinitrophenol potassium salt + benzyl 2,3-di-O-acetyl-6-O-para-methoxybenzyl-4-O-trifluoromethanesulfonyl-β-D-galactopyranoside (461026-22-2) → benzyl 2,3-di-O-acetyl-4-O-(3',4'-dinitrophenyl)-6-O-para-methoxybenzyl-β-D-glucopyranoside (461026-49-3)

Guidance literature:

In N,N-dimethyl-formamide; at 80 ℃; for 2.5h;

DOI:10.1021/ja020627c

Reference yield:

benzyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside (10343-13-2,30657-70-6,31281-76-2,53729-76-3,142696-63-7,83113-54-6) → benzyl 2,3-di-O-acetyl-4-O-(3',4'-dinitrophenyl)-6-O-para-methoxybenzyl-β-D-glucopyranoside (461026-49-3)

Guidance literature:

Multi-step reaction with 6 steps

1: NaOMe; MeOH / 20 °C

2: p-TsOH / dimethylformamide / 50 °C

3: pyridine / 20 °C

4: NaCNBH₃; TFA / tetrahydrofuran; CH₂Cl₂ / 19 h / 20 °C

5: pyridine / CH₂Cl₂ / -20 - 20 °C

6: 38 percent / dimethylformamide / 2.5 h / 80 °C

With pyridine; methanol; sodium methylate; sodium cyanoborohydride; toluene-4-sulfonic acid; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 1: Zemplen deacetylation;

DOI:10.1021/ja020627c

Reference yield:

D-galactose pentaacetate (25878-60-8) → benzyl 2,3-di-O-acetyl-4-O-(3',4'-dinitrophenyl)-6-O-para-methoxybenzyl-β-D-glucopyranoside (461026-49-3)

Guidance literature:

Multi-step reaction with 8 steps

1: HBr; AcOH / CH₂Cl₂ / 0 - 20 °C

2: 80 percent / Ag₂CO₃; I₂ / CH₂Cl₂ / 21 h

3: NaOMe; MeOH / 20 °C

4: p-TsOH / dimethylformamide / 50 °C

5: pyridine / 20 °C

6: NaCNBH₃; TFA / tetrahydrofuran; CH₂Cl₂ / 19 h / 20 °C

7: pyridine / CH₂Cl₂ / -20 - 20 °C

8: 38 percent / dimethylformamide / 2.5 h / 80 °C

With pyridine; methanol; hydrogen bromide; iodine; sodium methylate; sodium cyanoborohydride; toluene-4-sulfonic acid; acetic acid; silver carbonate; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 2: Koenigs-Knorr reaction / 3: Zemplen deacetylation;

DOI:10.1021/ja020627c

upstream raw materials:

benzyl 2,3-di-O-acetyl-6-O-para-methoxybenzyl-4-O-trifluoromethanesulfonyl-β-D-galactopyranoside

benzyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside

D-galactose pentaacetate

benzyl β-D-galactopyranoside

Downstream raw materials:

benzyl 4-O-(3',4'-dinitrophenyl)-β-D-glucopyranosiduronic acid

benzyl 4-O-(3',4'-dinitrophenyl)-β-D-glucopyranoside