4-Nitrophenyl beta-D-xyloside

Base Information

• Chemical Name: 4-Nitrophenyl beta-D-xyloside
• CAS No.: 2001-96-9
• Molecular Formula: C11H13NO7
• Molecular Weight: 271.227
• Hs Code.: 29400090
• European Community (EC) Number: 217-897-1
• DSSTox Substance ID: DTXSID801303045
• Nikkaji Number: J199.812I
• Wikidata: Q27162355
• Mol file: 2001-96-9.mol

Synonyms:4-nitrophenyl beta-D-xyloside;4-nitrophenyl beta-D-xyloside, (alpha-D)-isomer;4-nitrophenyl-alpha-D-xylopyranoside;p-nitrophenyl beta-D-xylopyranoside;p-nitrophenyl beta-D-xyloside;p-nitrophenylxyloside;para-nitrophenyl beta-D-xyloside;PNP xyloside;PNPX

Chemical Property of 4-Nitrophenyl beta-D-xyloside

Chemical Property:

• Appearance/Colour: off-white to pale yellow solid
• Vapor Pressure: 8.94E-12mmHg at 25°C
• Melting Point: 160 °C
• Refractive Index: 1.654
• Boiling Point: 523.2 °C at 760 mmHg
• PKA: 12.67±0.70(Predicted)
• Flash Point: 270.2 °C
• PSA: 124.97000
• Density: 1.597 g/cm³
• LogP: -0.06420
• Storage Temp.: −20°C
• Solubility.: methanol: 50 mg/mL, clear, faintly yellow
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 271.06920175
• Heavy Atom Count: 19
• Complexity: 313

Purity/Quality:

98%, ^*data from raw suppliers

p-Nitrophenyl b-D-Xylopyranoside ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(C(C(O1)OC2=CC=C(C=C2)[N+](=O)[O-])O)O)O
• Isomeric SMILES: C1[C@H]([C@@H]([C@H]([C@@H](O1)OC2=CC=C(C=C2)[N+](=O)[O-])O)O)O
• Uses: fluorescent probe for thiols, glutathione transferase substrate, substrate for colorimetric assay of pullulanase p-Nitrophenyl β-D-Xylopyranoside (cas# 2001-96-9) is a compound useful in organic synthesis.

Technology Process of 4-Nitrophenyl beta-D-xyloside

There total 19 articles about 4-Nitrophenyl beta-D-xyloside 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: 93.0%

1-O-(4-nitrophenyl)-2,3,4-tri-O-acetyl-β-D-xylopyranoside (24624-78-0,58902-46-8,67006-13-7,94921-62-7,94921-63-8,109526-97-8) → p-nitrophenyl β-D-xylopyranoside (2001-96-9)

Guidance literature:

With methanol; sodium methylate; for 5h; Ambient temperature;

DOI:10.1016/0008-6215(95)00214-E

Reference yield: 84.0%

p-nitrophenyl 4-O-(4'-O-acetylferuloyl)-2,3-di-O-acetyl-β-D-xylopyranoside (1235988-94-9) → p-nitrophenyl 4-O-feruloyl-β-D-xylopyranoside (637761-31-0) + p-nitrophenyl β-D-xylopyranoside (2001-96-9)

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: 84.0%

D-Xylose (87-72-9,608-45-7,608-46-8,608-47-9,2460-44-8,6748-95-4,6763-34-4,7261-26-9,7283-06-9,7283-07-0,7296-55-1,7296-56-2,7296-58-4,7296-59-5,7296-60-8,7296-61-9,7296-62-0,7322-30-7,10257-31-5,10257-32-6,10257-33-7,10257-34-8,10257-35-9,19982-83-3,20242-88-0,28697-53-2,36562-42-2,41546-41-2,89299-64-9,107655-34-5,115794-06-4,115794-07-5,130550-15-1,130606-21-2) + 4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) → p-nitrophenyl β-D-xylopyranoside (2001-96-9)

Guidance literature:

With 2-chloro-1,3-dimethylimidazolinium chloride; triethylamine; In water; at -10 ℃; for 1.16667h; stereoselective reaction;

DOI:10.1021/acs.orglett.0c00728

upstream raw materials:

4-nitro-phenol

2,3,4-tri-O-acetyl-α-L-arabinopyranosyl bromide

1-O-(4-nitrophenyl)-2,3,4-tri-O-acetyl-β-D-xylopyranoside

D-Xylose

Downstream raw materials:

4-nitrophenyl 4-O-chloroacetyl-β-D-xylopyranoside

p-Nitrophenyl 2,3-di-O-benzoyl-α-L-arabinopyranoside

4-nitrophenyl 2,3-di-O-benzoyl-4-O-chloroacetyl-β-D-xylopyranoside

4-nitrophenyl O-β-D-xylopyranosyl-(1<*>4)-bis4)>-β-D-xylopyranoside

Refernces

• 1、 -. "Propargyl-containing xylose and synthesis method thereof". Paragraph 0036; 0040. . Retrieved 2020/07/28.
• 2、 Fairbanks, Antony J.,Qiu, Xin. "Direct Synthesis of para-Nitrophenyl Glycosides from Reducing Sugars in Water". supporting information. . Retrieved 2020/03/24.