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

Base Information

• Chemical Name: methyl 1-(4-(tert-butyldimethylsilyloxy)methyl-2-nitrophenyl)-2,3,4-tri-O-acetyl-β-D-glucuronate
• CAS No.: 1353003-43-6
• Molecular Formula: C₂₆H₃₇NO₁₃Si
• Molecular Weight: 599.664
• Mol file: 1353003-43-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about methyl 1-(4-(tert-butyldimethylsilyloxy)methyl-2-nitrophenyl)-2,3,4-tri-O-acetyl-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%

tert-butyldimethylsilyl chloride (18162-48-6) + (25,3R,45,55,65)-2-(4-(hydroxymethyl)-2-nitrophenoxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (148579-94-6) → methyl 1-(4-(tert-butyldimethylsilyloxy)methyl-2-nitrophenyl)-2,3,4-tri-O-acetyl-β-D-glucuronate (1353003-43-6)

Guidance literature:

With 1H-imidazole; In dichloromethane; at 20 ℃; for 5h;

DOI:10.1002/cmdc.201100355

Reference yield: 90.0%

t-butyldimethylsiyl triflate (69739-34-0) + (25,3R,45,55,65)-2-(4-(hydroxymethyl)-2-nitrophenoxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (148579-94-6) → methyl 1-(4-(tert-butyldimethylsilyloxy)methyl-2-nitrophenyl)-2,3,4-tri-O-acetyl-β-D-glucuronate (1353003-43-6)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; for 0.0833333h;

Reference yield:

(2S,3R,4S,5S,6S)-2-(4-formyl-2-nitrophenoxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (148579-93-5) → methyl 1-(4-(tert-butyldimethylsilyloxy)methyl-2-nitrophenyl)-2,3,4-tri-O-acetyl-β-D-glucuronate (1353003-43-6)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium tetrahydroborate; silica gel / chloroform; isopropyl alcohol / Inert atmosphere

2: 1H-imidazole / N,N-dimethyl-formamide / Inert atmosphere

With 1H-imidazole; sodium tetrahydroborate; silica gel; In chloroform; N,N-dimethyl-formamide; isopropyl alcohol;

DOI:10.1021/np501004h

upstream raw materials:

tert-butyldimethylsilyl chloride

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

1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester

4-hydroxy-3-nitrobenzaldehyde

Downstream raw materials:

allyl 1-(4-(tert-butyldimethylsilyloxy)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

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

C₃₇H₄₀N₂O₁₉