4-NITROPHENYL-ALPHA-D-GLUCOPYRANOSIDE

Base Information

• Chemical Name: 4-NITROPHENYL-ALPHA-D-GLUCOPYRANOSIDE
• CAS No.: 3767-28-0
• Molecular Formula: C12H15NO8
• Molecular Weight: 301.253
• Hs Code.: 29389090
• European Community (EC) Number: 223-189-3
• DSSTox Substance ID: DTXSID701031992
• Nikkaji Number: J208.797I
• Wikidata: Q27163063
• ChEMBL ID: CHEMBL1235365
• Mol file: 3767-28-0.mol

Synonyms:Glucopyranoside,p-nitrophenyl, a-D-(8CI);a-D-Glucopyranoside, p-nitrophenyl(7CI);a-D-Glucoside, p-nitrophenyl(6CI);4-Nitrophenyl a-D-glucopyranoside;4-Nitrophenyl a-D-glucoside;4'-Nitrophenyl a-D-glucopyranoside;p-Nitrophenola-D-glucoside;p-Nitrophenyl a-D-glucopyranoside;p-Nitrophenyla-D-glucoside;

Chemical Property of 4-NITROPHENYL-ALPHA-D-GLUCOPYRANOSIDE

Chemical Property:

• Appearance/Colour: White crystals
• Vapor Pressure: 2.14E-14mmHg at 25°C
• Melting Point: 210-216 °C
• Refractive Index: 218.5 ° (C=0.5, H2O)
• Boiling Point: 582.2 °C at 760 mmHg
• PKA: 12.55±0.70(Predicted)
• Flash Point: 305.9 °C
• PSA: 145.20000
• Density: 1.599 g/cm³
• LogP: -0.70330
• Storage Temp.: 2-8°C
• Water Solubility.: Soluble in water, warm ethanol and methanol.
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 3
• Exact Mass: 301.07976644
• Heavy Atom Count: 21
• Complexity: 354

Purity/Quality:

98% ^*data from raw suppliers

p-Nitrophenyl-a-D-glucopyranoside ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=CC=C1[N+](=O)[O-])OC2C(C(C(C(O2)CO)O)O)O
• Isomeric SMILES: C1=CC(=CC=C1[N+](=O)[O-])O[C@@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O
• Uses: Substrate for a-glucosidase inhibitor Substrate for α-glucosidase inhibitor. p-Nitrophenyl α-D-Glucopyranoside is a substrate for α-glucosidase inhibitor.

Technology Process of 4-NITROPHENYL-ALPHA-D-GLUCOPYRANOSIDE

There total 24 articles about 4-NITROPHENYL-ALPHA-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: 51.0%

p-nitrophenyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside (14131-42-1) → 4-nitrophenyl-α-D-glucopyranoside (3767-28-0)

Guidance literature:

With sodium methylate; In methanol;

Reference yield: 28.0%

C12H14NO11S(1-)*Na(1+) → 4-nitrophenyl-α-D-glucopyranoside (3767-28-0)

Guidance literature:

With abalone sulfatase; In acetate buffer; at 37 ℃; for 75h; pH=6.8;

DOI:10.1016/j.carres.2004.03.026

Reference yield:

C42H65NO33 (74173-30-1,140694-63-9) → p-nitrophenyl-α-D-glucopyranosyl-(1→4)-O-α-D-glucopyranoside (3482-57-3,4419-94-7,7344-00-5,17400-77-0,56846-39-0,78248-67-6,80446-81-7) + 4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + 4-nitrophenyl α-maltotrioside (66451-58-9) + 4-nitrophenyl α-maltotetraoside (66068-37-9) + p‐nitrophenyl‐α‐D-maltopentoglycoside (66068-38-0) + 4-nitrophenyl-α-D-glucopyranoside (3767-28-0)

Guidance literature:

In water; at 35 ℃; Rate constant; Product distribution; acetate buffer pH 5.5, barley alpha-amylase 1 or 2;

DOI:10.1016/0008-6215(92)85080-J

upstream raw materials:

p-nitrophenyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside

C₄₂H₆₅NO₃₃

p-nitrophenyl α-maltoheptaoside

4-nitrophenyl α-maltotetraoside

Downstream raw materials:

p-nitrophenyl 2-O-β-D-mannopyranosyl-β-D-mannopyranoside

p-nitrophenyl 6-O-β-D-mannopyranosyl-β-D-mannopyranoside

p-nitrophenyl-α-D-glucopyranosyl-(1→4)-O-α-D-glucopyranoside

(2R,3R,4S,5S,6R)-2-[(2R,3R,4S,5R,6R)-3,5-Dihydroxy-2-hydroxymethyl-6-(4-nitro-phenoxy)-tetrahydro-pyran-4-yloxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

Refernces

• 1、 Fairbanks, Antony J.,Qiu, Xin. "Direct Synthesis of para-Nitrophenyl Glycosides from Reducing Sugars in Water". supporting information. . Retrieved 2020/03/24.
• 2、 De Winter, Karel,Desmet, Tom,Devlamynck, Tim,Van Renterghem, Lisa,Verhaeghe, Tom,Pelantova, Helena,Kren, Vladimir,Soetaert, Wim. "Biphasic catalysis with disaccharide phosphorylases: Chemoenzymatic synthesis of α- D -glucosides using sucrose phosphorylase". . p. 781 - 787. Retrieved 2014/07/08.