4-Nitrophenyl-ara

Base Information

• Chemical Name: 4-Nitrophenyl-ara
• CAS No.: 6892-58-6
• Molecular Formula: C₁₁H₁₃NO₇
• Molecular Weight: 271.227
• Hs Code.: 29400090
• Nikkaji Number: J419.918I
• Wikidata: Q27094128
• Metabolomics Workbench ID: 147727
• Mol file: 6892-58-6.mol

Synonyms:4-nitrophenyl-alpha-L-arabinofuranoside

Chemical Property of 4-Nitrophenyl-ara

Chemical Property:

• Appearance/Colour: white to slightly yellowish crystalline powder
• Vapor Pressure: 4.29E-13mmHg at 25°C
• Melting Point: 157-159℃
• Boiling Point: 553.7oC at 760 mmHg
• PKA: 12.77±0.70(Predicted)
• Flash Point: 288.7oC
• PSA: 124.97000
• Density: 1.562g/cm3
• LogP: -0.06420
• Storage Temp.: −20°C
• Solubility.: methanol: 50 mg/mL, clear, light yellow
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 3
• Exact Mass: 271.06920175
• Heavy Atom Count: 19
• Complexity: 313

Purity/Quality:

98%, ^*data from raw suppliers

4-Nitrophenyl a-L-arabinofuranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s): UN NO.
• Hazard Codes: UN NO.
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1[N+](=O)[O-])OC2C(C(C(O2)CO)O)O
• Isomeric SMILES: C1=CC(=CC=C1[N+](=O)[O-])O[C@H]2[C@@H]([C@H]([C@@H](O2)CO)O)O
• Uses: 4-Nitrophenyl-α-L-arabinofuranoside is a substrate for the enzyme arabinofuranosidase.

Technology Process of 4-Nitrophenyl-ara

There total 18 articles about 4-Nitrophenyl-ara 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: 91.0%

p-nitrophenyl 2,3,5-tri-O-benzoyl-α-L-arabinofuranoside (100645-43-0) → p-nitrophenyl α-L-arabinofuranoside (22796-65-2,59495-69-1,99676-56-9,6892-58-6)

Guidance literature:

With sodium hydroxide; In methanol;

DOI:10.1016/S0040-4039(02)02381-X

Reference yield: 85.0%

p-nitrophenyl 5-O-(4'-O-acetylferuloyl)-2,3-di-O-acetyl-α-L-arabinofuranoside (535960-67-9) → p-nitrophenyl α-L-arabinofuranoside (22796-65-2,59495-69-1,99676-56-9,6892-58-6) + 4-nitrophenyl 5-O-trans-feruloyl-α-L-arabinofuranoside

Guidance literature:

With di(n-butyl)tin oxide; In methanol; dichloromethane; for 6h; chemoselective reaction; Reflux;

DOI:10.1016/j.carres.2010.03.034

Reference yield: 79.0%

p-nitrophenyl 3-O-(4'-O-acetylferuloyl)-2,5-di-O-acetyl-α-L-arabinofuranoside (1235988-90-5) → p-nitrophenyl α-L-arabinofuranoside (22796-65-2,59495-69-1,99676-56-9,6892-58-6) + p-nitrophenyl 3-O-feruloyl-α-L-arabinofuranoside (943833-83-8)

Guidance literature:

With di(n-butyl)tin oxide; In methanol; dichloromethane; for 6h; chemoselective reaction; Reflux;

DOI:10.1016/j.carres.2010.03.034

upstream raw materials:

p-nitrophenyl 2,3,5-tri-O-benzoyl-α-L-arabinofuranoside

p-nitrophenyl 2,5-di-O-acetyl-α-L-arabinofuranoside

4-nitro-phenol

1,2,3,5-tetra-O-acetyl-L-arabinofuranose

Downstream raw materials:

allyl-α-L-arabinofuranoside

p-nitrophenyl 2-O-(4'-O-acetylferuloyl)-3,5-di-O-acetyl-α-L-arabinofuranoside

1-O-acetyl-2,3,5-tri-O-benzoyl-β-L-arabinofuranoside

2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl bromide

Refernces

• 1、 Mastihubova, Maria,Biely, Peter. "Preparation of regioselectively feruloylated p-nitrophenyl α-l-arabinofuranosides and β-d-xylopyranosides-convenient substrates for study of feruloyl esterase specificity". experimental part. p. 1094 - 1098. Retrieved 2010/09/12.
• 2、 Rémond, Caroline,Ferchichi, Mounir,Aubry, Nathalie,Plantier-Royon, Richard,Portella, Charles,O'Donohue, Michael J.. "Enzymatic synthesis of alkyl arabinofuranosides using a thermostable α-L-arabinofuranosidase". . p. 9653 - 9655. Retrieved 2007/10/03.