4-nitrophenyl 2-acetamido-2-deoxy-beta-D-galactopyranoside

Base Information

• Chemical Name: 4-nitrophenyl 2-acetamido-2-deoxy-beta-D-galactopyranoside
• CAS No.: 14948-96-0
• Molecular Formula: C14H18 N2 O8
• Molecular Weight: 342.306
• Hs Code.: 29329990
• European Community (EC) Number: 239-024-3
• DSSTox Substance ID: DTXSID201265021
• Nikkaji Number: J241.358B
• Wikidata: Q27104444
• Metabolomics Workbench ID: 52220
• Mol file: 14948-96-0.mol

Synonyms:4-nitrophenyl-2-acetamido-2-deoxygalactopyranoside;4-nitrophenyl-2-acetamido-2-deoxygalactopyranoside, (alpha)-isomer;4-nitrophenyl-N-acetyl-beta-D-galactosaminide;4-nitrophenyl-N-acetylamino-beta-galactose;para-nitrophenyl-N-acetyl-beta-D-galactosaminide;PNP-GalNAc;pNPGalNAc

Chemical Property of 4-nitrophenyl 2-acetamido-2-deoxy-beta-D-galactopyranoside

Chemical Property:

• Appearance/Colour: Off-white powder.
• Melting Point: 181 °C
• 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.: DMF: 50 mg/mL, clear, yellow-green
• 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

p-Nitrophenyl 2-Acetamido-2-deoxy- ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

Total 1 MSDS from other Authors

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
• Uses: p-Nitrophenyl 2-Acetamido-2-deoxy-β-D-galactopyranoside (cas# 14948-96-0) is a compound useful in organic synthesis.

Technology Process of 4-nitrophenyl 2-acetamido-2-deoxy-beta-D-galactopyranoside

There total 6 articles about 4-nitrophenyl 2-acetamido-2-deoxy-beta-D-galactopyranoside 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%

N-nitrophenyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-galactopyranoside (50271-51-7,13089-23-1) → p-nitrophenyl 2-acetamido-2-deoxy-β-D-galactopyranoside (14948-96-0,50645-66-4)

Guidance literature:

With methanol; sodium methylate; at 20 ℃; for 0.5h;

DOI:10.1016/j.carres.2007.05.023

Reference yield: 65.0%

4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + N-acetyl-D-galactosamine (72-87-7,1136-42-1,1136-44-3,6730-06-9,7772-94-3,10036-64-3,14131-60-3,14131-64-7,14131-68-1,14215-68-0,62057-49-2,62057-50-5,62057-51-6,62057-52-7,62057-53-8,62057-54-9,62057-55-0,62057-56-1,62075-50-7,62137-54-6,134451-97-1,134522-12-6,148347-16-4,6082-29-7) → p-nitrophenyl 2-acetamido-2-deoxy-β-D-galactopyranoside (14948-96-0,50645-66-4)

Guidance literature:

4-nitro-phenol; N-acetyl-D-galactosamine; With 2-chloro-1,3-dimethylimidazolinium chloride; triethylamine; In water; at -10 ℃; for 0.666667h; Sealed tube;

In water; at 80 ℃; stereoselective reaction; Sealed tube; Microwave irradiation;

DOI:10.1021/acs.orglett.0c00728

Reference yield:

4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) → p-nitrophenyl 2-acetamido-2-deoxy-β-D-galactopyranoside (14948-96-0,50645-66-4)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. NaOH solution; acetone

2: sodium methylate; methanol

With methanol; sodium hydroxide; sodium methylate; acetone;

upstream raw materials:

N-nitrophenyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-galactopyranoside

4-nitro-phenol

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

N-acetyl-D-galactosamine

Downstream raw materials:

4-nitrophenyl (β-D-galactopyranosyl)-(1->3)-2-acetamido-2-deoxy-β-D-galactopyranoside

4-nitrophenyl (β-D-glucopyranosyl)-(1->3)-2-acetamido-2-deoxy-β-D-galactopyranoside

Refernces

• 1、 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.