6-(2,4-Dinitrophenoxy)-5-fluoro-2-(hydroxymethyl)oxane-3,4-diol

Base Information

• Chemical Name: 6-(2,4-Dinitrophenoxy)-5-fluoro-2-(hydroxymethyl)oxane-3,4-diol
• CAS No.: 111495-86-4
• Molecular Formula: C12H13 F N2 O9
• Molecular Weight: 348.24
• Hs Code.: 29389090
• DSSTox Substance ID: DTXSID00399885
• Mol file: 111495-86-4.mol

Synonyms:6-(2,4-dinitrophenoxy)-5-fluoro-2-(hydroxymethyl)oxane-3,4-diol;2,4-dinitrophenyl-2-fluoro-2-deoxy-beta-D-glucopyranoside;SCHEMBL12697294;DTXSID00399885;(2R,3S,4S,5R,6S)-6-(2,4-dinitrophenoxy)-5-fluoro-2-(hydroxymethyl)oxane-3,4-diol;PD034504;FT-0667584;FT-0667590

Chemical Property of 6-(2,4-Dinitrophenoxy)-5-fluoro-2-(hydroxymethyl)oxane-3,4-diol

Chemical Property:

• Boiling Point: 615.7±55.0 °C(Predicted)
• PKA: 12.19±0.70(Predicted)
• PSA: 170.79000
• Density: 1.69±0.1 g/cm3(Predicted)
• LogP: 0.70530
• Storage Temp.: −20°C
• 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:

99%min ^*data from raw suppliers

2,4-Dinitrophenyl-2-deoxy-2-fluoro-b-D-glucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C=C1[N+](=O)[O-])[N+](=O)[O-])OC2C(C(C(C(O2)CO)O)O)F
• Uses: A glucosyl fluoride that can function as specific mechanism-based inactivators of glycosidases, and may have future application in the synthesis and degradation of oligosaccharide and polysaccharide.

Technology Process of 6-(2,4-Dinitrophenoxy)-5-fluoro-2-(hydroxymethyl)oxane-3,4-diol

There total 5 articles about 6-(2,4-Dinitrophenoxy)-5-fluoro-2-(hydroxymethyl)oxane-3,4-diol 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: 45.0%

2',4'-Dinitrophenyl 3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-β-D-glucopyranoside (111524-65-3) → 2,4-dinitrophenyl-2-fluoro-2-deoxy-β-D-glucopyranoside (111495-86-4)

Guidance literature:

With methanol; acetyl chloride; at 0 - 20 ℃;

DOI:10.1021/ja992044h

Reference yield:

2,4-Dinitrofluorobenzene (70-34-8,65727-75-5) → 2,4-dinitrophenyl-2-fluoro-2-deoxy-β-D-glucopyranoside (111495-86-4)

Guidance literature:

Multi-step reaction with 2 steps

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

1.2: dimethylformamide / 1.5 h / 20 °C

2.1: 45 percent / acetyl chloride; methanol / 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-glucopyranose (226382-59-8) → 2,4-dinitrophenyl-2-fluoro-2-deoxy-β-D-glucopyranoside (111495-86-4)

Guidance literature:

Multi-step reaction with 2 steps

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

1.2: dimethylformamide / 1.5 h / 20 °C

2.1: 45 percent / acetyl chloride; methanol / 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

upstream raw materials:

2',4'-Dinitrophenyl 3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-β-D-glucopyranoside

2,4-Dinitrofluorobenzene

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

3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-α-D-glucopyranosyl bromide

Downstream raw materials:

2,4-dinitrophenyl 2-deoxy-2-fluoro-β-cellobioside

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.