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

Base Information

• Chemical Name: allyl 1-(4-(tert-butyldimethylsilyloxy)methyl-2-nitrophenyl)-2,3,4-tri-O-allyloxycarbonyl-β-D-glucuronate
• CAS No.: 1353003-46-9
• Molecular Formula: C₃₄H₄₅NO₁₆Si
• Molecular Weight: 751.814
• Mol file: 1353003-46-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about allyl 1-(4-(tert-butyldimethylsilyloxy)methyl-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: 82.0%

allyl 1-(4-(tert-butyldimethylsilyloxy)methyl-2-nitrophenyl)-β-D-glucuronate (1353003-45-8) + Allyl chloroformate (2937-50-0) → allyl 1-(4-(tert-butyldimethylsilyloxy)methyl-2-nitrophenyl)-2,3,4-tri-O-allyloxycarbonyl-β-D-glucuronate (1353003-46-9)

Guidance literature:

With pyridine; at 0 - 20 ℃; for 72h; Inert atmosphere;

DOI:10.1002/chem.202003471

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-(tert-butyldimethylsilyloxy)methyl-2-nitrophenyl)-2,3,4-tri-O-allyloxycarbonyl-β-D-glucuronate (1353003-46-9)

Guidance literature:

Multi-step reaction with 3 steps

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

2: allyl alcohol / 1 h / 20 °C

3: pyridine / 24 h / 20 °C

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

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-(tert-butyldimethylsilyloxy)methyl-2-nitrophenyl)-2,3,4-tri-O-allyloxycarbonyl-β-D-glucuronate (1353003-46-9)

Guidance literature:

Multi-step reaction with 4 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

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

DOI:10.1002/cmdc.201100355

upstream raw materials:

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

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

Allyl chloroformate

(25,3R,45,55,65)-2-(4-(hydroxymethyl)-2-nitrophenoxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Downstream raw materials:

C₅₁H₄₆N₄O₂₇

C₃₇H₄₀N₂O₁₉

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

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