2,4-Dinitrophenyl 2-Deoxy-2-fluoro-β-D-galactoside 3,4,6-Triacetate

Base Information

• Chemical Name: 2,4-Dinitrophenyl 2-Deoxy-2-fluoro-β-D-galactoside 3,4,6-Triacetate
• CAS No.: 207975-84-6
• Molecular Formula: C18H19FN2O12
• Molecular Weight: 474.3480632
• Mol file: 207975-84-6.mol

Synonyms:2,4-Dinitrophenyl 2-Deoxy-2-fluoro-β-D-galactoside 3,4,6-Triacetate;2,4-Dinitrophenyl 2-deoxy-2-fluoro-β-D-galactopyranoside 3,4,6-Triacetate

Chemical Property of 2,4-Dinitrophenyl 2-Deoxy-2-fluoro-β-D-galactoside 3,4,6-Triacetate

Chemical Property:

• PSA: 189.00000
• LogP: 2.41770
• Storage Temp.: -20°C Freezer
• Solubility.: Dichloromethane, Ethyl Acetate

Purity/Quality:

98% ^*data from raw suppliers

2,4-Dinitrophenyl2-Deoxy-2-fluoro-β-D-galactoside3,4,6-Triacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 2,4-Dinitrophenyl 2-Deoxy-2-fluoro-β-D-galactoside 3,4,6-Triacetate (cas# 207975-84-6) is a compound useful in organic synthesis.

Technology Process of 2,4-Dinitrophenyl 2-Deoxy-2-fluoro-β-D-galactoside 3,4,6-Triacetate

There total 5 articles about 2,4-Dinitrophenyl 2-Deoxy-2-fluoro-β-D-galactoside 3,4,6-Triacetate 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: 61.0%

sodium 2,4-dinitrophenoxide (1011-73-0) + 1-(3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-α-D-galactopyranosyl)-4-chloromethyl-1,4-diazonia-bicyclo[2.2.2]octane bis(tetrafluoroborate) → 2,4-dinitrophenyl-3,4,6-tri-O-acetyl-2-fluoro-2-deoxy-β-D-galactopyranoside (207975-84-6)

Guidance literature:

In acetonitrile; Heating;

DOI:10.1016/S0040-4020(98)00189-6

Reference yield: 42.0%

2,4-Dinitrofluorobenzene (70-34-8,65727-75-5) + 3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-D-galactopyranoside (108794-37-2,108794-38-3,108794-41-8,108794-42-9) → 2,4-dinitrophenyl-3,4,6-tri-O-acetyl-2-fluoro-2-deoxy-α-D-galactopyranoside + 2,4-dinitrophenyl-3,4,6-tri-O-acetyl-2-fluoro-2-deoxy-β-D-galactopyranoside (207975-84-6)

Guidance literature:

3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-D-galactopyranoside; With 1,4-diaza-bicyclo[2.2.2]octane; In N,N-dimethyl-formamide; at 20 ℃;

2,4-Dinitrofluorobenzene; In N,N-dimethyl-formamide; at 20 ℃;

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-3,4,6-tri-O-acetyl-2-fluoro-2-deoxy-β-D-galactopyranoside (207975-84-6)

Guidance literature:

Multi-step reaction with 3 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

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

DOI:10.1021/ja992044h

upstream raw materials:

sodium 2,4-dinitrophenoxide

2,4-Dinitrofluorobenzene

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

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

Downstream raw materials:

2,4-dinitrophenyl-2-fluoro-2-deoxy-β-D-galactopyranoside

Refernces

• 1、 Namchuk, Mark N.,McCarter, John D.,Becalski, Adam,Andrews, Trevor,Withers, Stephen G.. "The role of sugar substituents in glycoside hydrolysis". . p. 1270 - 1277. Retrieved 2007/10/03.