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

Base Information

• Chemical Name: benzyl 4-O-(3',4'-dinitrophenyl)-β-D-glucopyranosiduronic acid
• CAS No.: 461026-26-6
• Molecular Formula: C₁₉H₁₈N₂O₁₁
• Molecular Weight: 450.359
• Mol file: 461026-26-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 10 articles about benzyl 4-O-(3',4'-dinitrophenyl)-β-D-glucopyranosiduronic acid 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: 85.0%

benzyl 4-O-(3',4'-dinitrophenyl)-β-D-glucopyranoside (461026-24-4) → benzyl 4-O-(3',4'-dinitrophenyl)-β-D-glucopyranosiduronic acid (461026-26-6)

Guidance literature:

With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium bromide; tetrabutylammomium bromide; sodium hydrogencarbonate; In methanol; ethyl acetate; at 0 ℃; 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 4-O-(3',4'-dinitrophenyl)-β-D-glucopyranosiduronic acid (461026-26-6)

Guidance literature:

Multi-step reaction with 8 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

7: 82 percent / AcCl; MeOH / 4 °C

8: 85 percent / 2,2,6,6-tetramethyl-1-piperidinyloxyl; NaOCl; NaBr / TBAB; NaHCO₃ / ethyl acetate; methanol / 2.5 h / 0 °C

With pyridine; methanol; sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium methylate; sodium cyanoborohydride; toluene-4-sulfonic acid; acetyl chloride; trifluoroacetic acid; sodium bromide; tetrabutylammomium bromide; sodium hydrogencarbonate; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 1: Zemplen deacetylation;

DOI:10.1021/ja020627c

Reference yield:

D-galactose pentaacetate (25878-60-8) → benzyl 4-O-(3',4'-dinitrophenyl)-β-D-glucopyranosiduronic acid (461026-26-6)

Guidance literature:

Multi-step reaction with 10 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

9: 82 percent / AcCl; MeOH / 4 °C

10: 85 percent / 2,2,6,6-tetramethyl-1-piperidinyloxyl; NaOCl; NaBr / TBAB; NaHCO₃ / ethyl acetate; methanol / 2.5 h / 0 °C

With pyridine; methanol; sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; hydrogen bromide; iodine; sodium methylate; sodium cyanoborohydride; toluene-4-sulfonic acid; acetic acid; acetyl chloride; silver carbonate; trifluoroacetic acid; sodium bromide; tetrabutylammomium bromide; sodium hydrogencarbonate; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 2: Koenigs-Knorr reaction / 3: Zemplen deacetylation;

DOI:10.1021/ja020627c

upstream raw materials:

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

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

D-galactose pentaacetate

benzyl alcohol

Downstream raw materials:

3,4-dinitophenol