allyl 1-(4-hydroxymethyl-2-nitrophenyl)-2,3,4-tri-O-allyloxycarbonyl-β-D-glucuronate

Base Information

• Chemical Name: allyl 1-(4-hydroxymethyl-2-nitrophenyl)-2,3,4-tri-O-allyloxycarbonyl-β-D-glucuronate
• CAS No.: 1353003-35-6
• Molecular Formula: C₂₈H₃₁NO₁₆
• Molecular Weight: 637.551
• Mol file: 1353003-35-6.mol

Synonyms:allyl 1-(4-hydroxymethyl-2-nitrophenyl)-2,3,4-tri-O-allyloxycarbonyl-β-D-glucuronate

Chemical Property of allyl 1-(4-hydroxymethyl-2-nitrophenyl)-2,3,4-tri-O-allyloxycarbonyl-β-D-glucuronate

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of allyl 1-(4-hydroxymethyl-2-nitrophenyl)-2,3,4-tri-O-allyloxycarbonyl-β-D-glucuronate

There total 8 articles about allyl 1-(4-hydroxymethyl-2-nitrophenyl)-2,3,4-tri-O-allyloxycarbonyl-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: 95.0%

allyl 1-(4-(tert-butyldimethylsilyloxy)methyl-2-nitrophenyl)-2,3,4-tri-O-allyloxycarbonyl-β-D-glucuronate (1353003-46-9) → allyl 1-(4-hydroxymethyl-2-nitrophenyl)-2,3,4-tri-O-allyloxycarbonyl-β-D-glucuronate (1353003-35-6)

Guidance literature:

With pyridine hydrogenfluoride; at 20 ℃; for 1h;

DOI:10.1002/cmdc.201100355

Reference yield:

(25,3R,45,55,65)-2-(4-(hydroxymethyl)-2-nitrophenoxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (148579-94-6) → allyl 1-(4-hydroxymethyl-2-nitrophenyl)-2,3,4-tri-O-allyloxycarbonyl-β-D-glucuronate (1353003-35-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 1H-imidazole / dichloromethane / 5 h / 20 °C

2: methanol; sodium methylate / tetrahydrofuran / 2 h / 0 °C

3: allyl alcohol / 1 h / 20 °C

4: pyridine / 24 h / 20 °C

5: pyridine hydrogenfluoride / 1 h / 20 °C

With pyridine; 1H-imidazole; methanol; sodium methylate; pyridine hydrogenfluoride; In tetrahydrofuran; dichloromethane; allyl alcohol;

DOI:10.1002/cmdc.201100355

Reference yield:

methyl 1-(4-(tert-butyldimethylsilyloxy)methyl-2-nitrophenyl)-2,3,4-tri-O-acetyl-β-D-glucuronate (1353003-43-6) → allyl 1-(4-hydroxymethyl-2-nitrophenyl)-2,3,4-tri-O-allyloxycarbonyl-β-D-glucuronate (1353003-35-6)

Guidance literature:

Multi-step reaction with 4 steps

1: methanol; sodium methylate / tetrahydrofuran / 2 h / 0 °C

2: allyl alcohol / 1 h / 20 °C

3: pyridine / 24 h / 20 °C

4: pyridine hydrogenfluoride / 1 h / 20 °C

With pyridine; methanol; sodium methylate; pyridine hydrogenfluoride; In tetrahydrofuran; allyl alcohol;

DOI:10.1002/cmdc.201100355

upstream raw materials:

allyl 1-(4-(tert-butyldimethylsilyloxy)methyl-2-nitrophenyl)-2,3,4-tri-O-allyloxycarbonyl-β-D-glucuronate

methyl 1-(4-(tert-butyldimethylsilyloxy)methyl-2-nitrophenyl)-2,3,4-tri-O-acetyl-β-D-glucuronate

C₂₀H₃₁NO₁₀Si

allyl 1-(4-(tert-butyldimethylsilyloxy)methyl-2-nitrophenyl)-β-D-glucuronate

Downstream raw materials:

C₃₇H₄₀N₂O₁₉

C₅₁H₄₆N₄O₂₇

allyl 1-(4-(O-4-nitrophenyloxycarbonyl)methyl-2-nitrophenyl)-2,3,4-tri-O-allyloxycarbonyl-β-D-glucuronate