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

Base Information

• Chemical Name: allyl 1-(4-(tert-butyldimethylsilyloxy)methyl-2-nitrophenyl)-β-D-glucuronate
• CAS No.: 1353003-45-8
• Molecular Formula: C₂₂H₃₃NO₁₀Si
• Molecular Weight: 499.59
• Mol file: 1353003-45-8.mol

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

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

There total 7 articles about allyl 1-(4-(tert-butyldimethylsilyloxy)methyl-2-nitrophenyl)-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: 83.0%

C20H31NO10Si (1353003-44-7) + sodium allyloxide (20907-32-8) → allyl 1-(4-(tert-butyldimethylsilyloxy)methyl-2-nitrophenyl)-β-D-glucuronate (1353003-45-8)

Guidance literature:

at 0 - 20 ℃; for 0.666667h; Inert atmosphere;

DOI:10.1002/chem.202003471

Reference yield: 51.0%

methyl 1-(4-(tert-butyldimethylsilyloxy)methyl-2-nitrophenyl)-2,3,4-tri-O-acetyl-β-D-glucuronate (1353003-43-6) + allyl alcohol (107-18-6) → allyl 1-(4-(tert-butyldimethylsilyloxy)methyl-2-nitrophenyl)-β-D-glucuronate (1353003-45-8)

Guidance literature:

methyl 1-(4-(tert-butyldimethylsilyloxy)methyl-2-nitrophenyl)-2,3,4-tri-O-acetyl-β-D-glucuronate; With sodium methylate; In methanol; Inert atmosphere;

allyl alcohol; With sodium; Inert atmosphere;

DOI:10.1021/np501004h

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)-β-D-glucuronate (1353003-45-8)

Guidance literature:

Multi-step reaction with 3 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

With 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

C₂₀H₃₁NO₁₀Si

sodium allyloxide

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

Downstream raw materials:

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

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

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