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

Base Information

Chemical Name:2',4'-Dinitrophenyl-2,3,6-tri-O-acetyl-4-deoxy-4-fluoro-β-D-glucopyranoside
CAS No.:114928-22-2
Molecular Formula:C₁₈H₁₉FN₂O₁₂
Molecular Weight:474.353
Hs Code.:

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

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

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

There total 4 articles about 2',4'-Dinitrophenyl-2,3,6-tri-O-acetyl-4-deoxy-4-fluoro-β-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: 32.0%

: Acetic acid (2R,3R,4R,5R,6R)-3-acetoxy-6-acetoxymethyl-5-fluoro-2-hydroxy-tetrahydro-pyran-4-yl ester

: 70-34-8,65727-75-5
2,4-Dinitrofluorobenzene

: 114928-22-2
2',4'-Dinitrophenyl-2,3,6-tri-O-acetyl-4-deoxy-4-fluoro-β-D-glucopyranoside

Guidance literature:: Acetic acid (2R,3R,4R,5R,6R)-3-acetoxy-6-acetoxymethyl-5-fluoro-2-hydroxy-tetrahydro-pyran-4-yl ester; 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 ℃; for 3h; Further stages.;
DOI:10.1021/ja992044h

Reference yield:

: 27108-07-2
(2S,3R,4R,5R,6R)-6-(acetoxymethyl)-5-fluorotetrahydro-2H-pyran-2,3,4-triyl triacetate

: 114928-22-2
2',4'-Dinitrophenyl-2,3,6-tri-O-acetyl-4-deoxy-4-fluoro-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1.1: 88 percent / 2-aminoethanol / ethyl acetate / 20 °C

2.1: 1,4-diazabicyclo[2.2.2]octane / dimethylformamide / 20 °C

2.2: 32 percent / dimethylformamide / 3 h / 20 °C

With 1,4-diaza-bicyclo[2.2.2]octane; ethanolamine; In ethyl acetate; N,N-dimethyl-formamide; 1.1: Deacetylation / 2.1: deprotonation / 2.2: Substitution;
DOI:10.1021/ja992044h

Reference yield:

: 130818-74-5
(2R,3R,4R,5R,6R)-6-(acetoxymethyl)-2-bromo-5-fluorotetrahydro-2H-pyran-3,4-diyl diacetate

: 114928-22-2
2',4'-Dinitrophenyl-2,3,6-tri-O-acetyl-4-deoxy-4-fluoro-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: 64 mg / Ag₂CO₃, H₂O / acetone / 20 h / Ambient temperature

2: 45 mg

With water; silver carbonate; In acetone;
DOI:10.1139/v90-288