2-Nitrophenyl beta-D-glucopyranoside

Base Information

• Chemical Name: 2-Nitrophenyl beta-D-glucopyranoside
• CAS No.: 2816-24-2
• Molecular Formula: C12H15NO8
• Molecular Weight: 301.253
• Hs Code.: 29400090
• European Community (EC) Number: 220-568-5
• DSSTox Substance ID: DTXSID901300913
• Nikkaji Number: J306.754H
• ChEMBL ID: CHEMBL4442376
• Mol file: 2816-24-2.mol

Synonyms:2-nitrophenyl-beta-D-glucopyranoside;2-NP-beta-Glc;ortho-nitrophenyl-beta-D-glucopyranoside

Chemical Property of 2-Nitrophenyl beta-D-glucopyranoside

Chemical Property:

• Appearance/Colour: white to yellow powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 141-142℃
• Refractive Index: 1.648
• Boiling Point: 572.4 °C at 760 mmHg
• PKA: 12.69±0.70(Predicted)
• Flash Point: 300 °C
• PSA: 145.20000
• Density: 1.599 g/cm³
• LogP: -0.70330
• Storage Temp.: 2-8°C
• Solubility.: Methanol (Slightly), Water (Slightly)
• Water Solubility.: Soluble in water
• XLogP3: -1.2
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 3
• Exact Mass: 301.07976644
• Heavy Atom Count: 21
• Complexity: 362

Purity/Quality:

98%, ^*data from raw suppliers

2-Nitrophenyl b-D-glucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C(=C1)[N+](=O)[O-])OC2C(C(C(C(O2)CO)O)O)O
• Isomeric SMILES: C1=CC=C(C(=C1)[N+](=O)[O-])O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O
• Uses: 2-Nitrophenyl b-D-Glucopyranoside is used in preparation of phenol glycosides and their use in treatment of urolithiasis.

Technology Process of 2-Nitrophenyl beta-D-glucopyranoside

There total 21 articles about 2-Nitrophenyl beta-D-glucopyranoside 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: 75.0%

D-Glucose (2280-44-6) + 2-hydroxynitrobenzene (88-75-5,78813-12-4) → 2-nitrophenyl β-D-glucopyranoside (2816-24-2)

Guidance literature:

D-Glucose; 2-hydroxynitrobenzene; With triethylamine; In water; at 20 ℃; for 0.166667h;

With 2-chloro-1,3-dimethylimidazolinium chloride; triethylamine; In water; at -10 ℃; for 1h;

DOI:10.1039/d0ob01727b

Reference yield: 22.0%

(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(2-nitrophenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate (14581-85-2) → o-nitrophenyl 2-O-acetyl-β-D-glucopyranoside + 2-nitrophenyl β-D-glucopyranoside (2816-24-2)

Guidance literature:

With hydrogenchloride; In ethanol; chloroform; water; at 30 ℃; for 12h; regioselective reaction; Kinetics;

DOI:10.1016/j.carres.2018.02.003

Reference yield:

(2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(2-nitrophenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate (3053-17-6) → o-nitrophenyl D-galactopyranoside (2816-24-2,18249-33-7,19710-96-4,19887-85-5,56193-44-3,81132-76-5,118014-27-0,118396-84-2,369-07-3)

Guidance literature:

With methanol; barium methoxide;

DOI:10.1021/ja01165a601

upstream raw materials:

(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(2-nitrophenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate

2-hydroxynitrobenzene

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

2,3,4,6-tetra-O-benzoylglucosyl bromide

Downstream raw materials:

o-nitrophenyl 2,3,6-tri-O-benzoyl-α-D-galactopyranoside

1-(4-hydroxyphenyl)-3'-oxopropyl-β-D-glucopyranose

2-hydroxynitrobenzene

D-Glucose

Refernces

• 1、 Stepanova, Elena V.,Nagornaya, Marina O.,Filimonov, Victor D.,Valiev, Rashid R.,Belyanin, Maxim L.,Drozdova, Anna K.,Cherepanov, Victor N.. "A new look at acid catalyzed deacetylation of carbohydrates: A regioselective synthesis and reactivity of 2-O-acetyl aryl glycopyranosides". . p. 60 - 66. Retrieved 2018/02/20.
• 2、 Giguere, Denis,Sato, Sachiko,St-Pierre, Christian,Sirois, Suzanne,Roy, Rene. "Aryl O- and S-galactosides and lactosides as specific inhibitors of human galectins-1 and -3: Role of electrostatic potential at O-3". . p. 1668 - 1672. Retrieved 2007/10/03.