4-Nitrophenyl 2-acetamido-2-deoxy-beta-D-glucopyranoside

Base Information

• Chemical Name: 4-Nitrophenyl 2-acetamido-2-deoxy-beta-D-glucopyranoside
• CAS No.: 3459-18-5
• Molecular Formula: C14H18N2O8
• Molecular Weight: 342.306
• Hs Code.: 29329990
• European Community (EC) Number: 222-398-7
• UNII: GVY9AA7Y5C
• DSSTox Substance ID: DTXSID301275049
• Nikkaji Number: J216.131A
• Wikidata: Q27162478
• ChEMBL ID: CHEMBL595014
• Mol file: 3459-18-5.mol

Synonyms:4-nitrophenyl N-acetyl-beta-D-glucosaminide;4-nitrophenyl N-acetylglucosamine;4-nitrophenyl-2-acetamido-2-deoxy-beta-D-glucopyranoside;4-nitrophenyl-N-acetyl-2-deoxyglucopyranoside;4-nitrophenyl-N-acetyl-2-deoxyglucopyranoside, (alpha)-isomer;4-nitrophenyl-N-acetyl-beta-D-glucopyranoside;4-nitrophenyl-N-acetylglucosamine;NP-GlcNAc;p-nitrophenyl-N-acetyl-beta-D-glucopyranoside;para-nitrophenyl-N-acetyl-beta-D-glucopyranoside;PNP-GlcNAc;pNPGlcNAc

Chemical Property of 4-Nitrophenyl 2-acetamido-2-deoxy-beta-D-glucopyranoside

Chemical Property:

• Appearance/Colour: slightly off-white crystalline solid
• Melting Point: 210-212 °C
• Refractive Index: 1.5110 (estimate)
• Boiling Point: 694.7 °C at 760 mmHg
• PKA: 12.76±0.70(Predicted)
• Flash Point: 374 °C
• PSA: 154.07000
• Density: 1.51 g/cm³
• LogP: -0.16860
• Storage Temp.: −20°C
• Solubility.: H2O: 5 mg/mL, clear, colorless to very faintly yellow
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 342.10631554
• Heavy Atom Count: 24
• Complexity: 449

Purity/Quality:

98%, ^*data from raw suppliers

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

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC1C(C(C(OC1OC2=CC=C(C=C2)[N+](=O)[O-])CO)O)O
• Isomeric SMILES: CC(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@H]1OC2=CC=C(C=C2)[N+](=O)[O-])CO)O)O
• Recent EU Clinical Trials: Translational stem cell research in ophthalmology - regenerating the anterior cornea through standardized transplantation of limbal epithelial stem cells: a phase II multicenter trial
• Uses: 4-Nitrophenyl-N-acetyl-β- D-glucosaminide is a useful substrate for the rapid colorimetric assay of N-Acetyl-beta-glucosaminidase in human urine substrate for a-L-fucosidases

Technology Process of 4-Nitrophenyl 2-acetamido-2-deoxy-beta-D-glucopyranoside

There total 16 articles about 4-Nitrophenyl 2-acetamido-2-deoxy-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: 100.0%

p-nitrophenyl 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranoside (13089-27-5,13089-23-1) → 4-nitrophenyl N-acetyl-β-D-glucosaminide (3459-18-5,50645-66-4)

Guidance literature:

With sodium methylate; In methanol;

DOI:10.1039/c39910000536

Reference yield: 99.0%

C20H24N2O11 (13089-23-1) → 4-nitrophenyl N-acetyl-β-D-glucosaminide (3459-18-5,50645-66-4)

Guidance literature:

With methanol; sodium methylate; at 20 ℃; for 2h;

Reference yield: 92.0%

→ 4-nitrophenyl N-acetyl-β-D-glucosaminide (3459-18-5,50645-66-4)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 0.25h;

upstream raw materials:

p-nitrophenyl 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranoside

p-Nitrophenyl penta-N-acetyl-β-chitopentaoside

4-nitrophenol sodium salt

Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester

Downstream raw materials:

β-D-GlcpNAc-(1->6)-α-D-Manp-OMe

methyl-N,N'-diacetyl-β-chitobioside

methyl 2-acetamido-4-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-2-deoxy-D-α-glucopyranoside

4-O-(2-Acetamido-2-deoxy-β-D-glucopyranosyl)-D-mannose

Refernces

• 1、 -. "NOVEL IMMUNODULATING SMALL MOLECULES". Paragraph 0188; 0193. . Retrieved 2020/01/31.
• 2、 Fairbanks, Antony J.,Qiu, Xin. "Scope of the DMC mediated glycosylation of unprotected sugars with phenols in aqueous solution". . p. 7355 - 7365. Retrieved 2020/10/13.