2',4'-Dinitrophenyl 2-deoxy-2-fluorogalactopyranoside

Base Information

• Chemical Name: 2',4'-Dinitrophenyl 2-deoxy-2-fluorogalactopyranoside
• CAS No.: 143716-62-5
• Molecular Formula: C12H13 F N2 O9
• Molecular Weight: 348.24
• DSSTox Substance ID: DTXSID10162527
• Nikkaji Number: J863.085B
• Wikidata: Q83031218
• Mol file: 143716-62-5.mol

Synonyms:2',4'-dinitrophenyl 2-deoxy--2-fluoro-beta-D-galactopyranoside;2',4'-dinitrophenyl 2-deoxy-2-fluorogalactopyranoside;dinitroPh-DFGP

Chemical Property of 2',4'-Dinitrophenyl 2-deoxy-2-fluorogalactopyranoside

Chemical Property:

• Melting Point: 168-170°C
• Boiling Point: 615.7°Cat760mmHg
• Flash Point: 326.2°C
• PSA: 170.79000
• Density: 1.69g/cm³
• LogP: 0.70530
• Storage Temp.: Amber Vial, Refrigerator
• Solubility.: Methanol (Slightly)
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 3
• Exact Mass: 348.06050816
• Heavy Atom Count: 24
• Complexity: 470

Purity/Quality:

97% ^*data from raw suppliers

2,4-Dinitrophenyl2-Deoxy-2-fluoro-β-D-galactoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC(=C(C=C1[N+](=O)[O-])[N+](=O)[O-])OC2C(C(C(C(O2)CO)O)O)F
• Isomeric SMILES: C1=CC(=C(C=C1[N+](=O)[O-])[N+](=O)[O-])O[C@H]2[C@@H]([C@H]([C@H]([C@H](O2)CO)O)O)F
• Uses: Fluorinated and deoxygenated glycosides as mechanistic probes of Escherichia coli (lacZ) β-galactosidase. By use of the slow substrate 2,4-dinitrophenyl-2-deoxy-2-fluoro-β-D-galactopyranoside, a glycosyl enzyme intermediate has been trapped on the enzyme. Glu-268 was identified as the catalytic nucleophile of human lysosomal β-galactosidase precursor. 2',4'-Dinitrophenyl 2-deoxy-2-fluorogalactopyranoside is fluorinated and deoxygenated glycosides as mechanistic probes of Escherichia coli (lacZ) β-galactosidase. By use of the slow substrate 2,4-dinitrophenyl-2-deoxy-2-fluoro-β-D-galactopyranoside, a glycosyl enzyme intermediate has been trapped on the enzyme.

Technology Process of 2',4'-Dinitrophenyl 2-deoxy-2-fluorogalactopyranoside

There total 5 articles about 2',4'-Dinitrophenyl 2-deoxy-2-fluorogalactopyranoside 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%

2,4-dinitrophenyl-3,4,6-tri-O-acetyl-2-fluoro-2-deoxy-β-D-galactopyranoside (207975-84-6) → 2,4-dinitrophenyl-2-fluoro-2-deoxy-β-D-galactopyranoside (143716-62-5)

Guidance literature:

With methanol; acetyl chloride; at 0 - 20 ℃; for 33h;

DOI:10.1021/ja992044h

Reference yield:

2,4-Dinitrofluorobenzene (70-34-8,65727-75-5) → 2,4-dinitrophenyl-2-fluoro-2-deoxy-β-D-galactopyranoside (143716-62-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 1,4-diazabicyclo[2.2.2]octane / dimethylformamide / 20 °C

1.2: 42 percent / dimethylformamide / 20 °C

2.1: 51 percent / acetyl chloride; methanol / 33 h / 0 - 20 °C

With 1,4-diaza-bicyclo[2.2.2]octane; methanol; acetyl chloride; In N,N-dimethyl-formamide; 1.1: deprotonation / 1.2: Substitution / 2.1: Deacetylation;

DOI:10.1021/ja992044h

Reference yield:

3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-β-D-galactopyranosyl fluoride (75414-44-7) → 2,4-dinitrophenyl-2-fluoro-2-deoxy-β-D-galactopyranoside (143716-62-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: HBr / acetic acid

2.1: 0.32 g / Ag₂CO₃ / acetone; H₂O / 25 h / 0 - 24 °C

3.1: 1,4-diazabicyclo[2.2.2]octane / dimethylformamide / 20 °C

3.2: 42 percent / dimethylformamide / 20 °C

4.1: 51 percent / acetyl chloride; methanol / 33 h / 0 - 20 °C

With 1,4-diaza-bicyclo[2.2.2]octane; methanol; hydrogen bromide; acetyl chloride; silver carbonate; In water; acetic acid; N,N-dimethyl-formamide; acetone; 1.1: Substitution / 2.1: catalyzed hydrolysis / 3.1: deprotonation / 3.2: Substitution / 4.1: Deacetylation;

DOI:10.1021/ja992044h

upstream raw materials:

2,4-dinitrophenyl-3,4,6-tri-O-acetyl-2-fluoro-2-deoxy-β-D-galactopyranoside

2,4-Dinitrofluorobenzene

3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-β-D-galactopyranosyl fluoride

3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-D-galactopyranoside