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

Base Information

• Chemical Name: 2',4'-Dinitrophenyl 3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-α-D-glucopyranoside
• CAS No.: 111524-64-2
• Molecular Formula: C₁₈H₁₉FN₂O₁₂
• Molecular Weight: 474.353

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

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

Chemical Property:

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

There total 5 articles about 2',4'-Dinitrophenyl 3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-α-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: 15.1%

2,4-Dinitrofluorobenzene (70-34-8,65727-75-5) + 3,4,6-tri-O-acetyl-2-deoxy-2-fluor-D-glucopyranose → 2,4-dinitrophenyl-3,4,6-tri-O-acetyl-2-fluoro-2-deoxy-β-D-mannopyranoside (262607-45-4) + 2',4'-Dinitrophenyl 3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-β-D-glucopyranoside (111524-65-3) + 2',4'-Dinitrophenyl 3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-α-D-glucopyranoside (111524-64-2) + 2,4-dinitrophenyl-3,4,6-tri-O-acetyl-2-fluoro-2-deoxy-α-D-mannopyranoside

Guidance literature:

With 1,4-diaza-bicyclo[2.2.2]octane; In N,N-dimethyl-formamide; at 20 ℃; optical yield given as %de; Inert atmosphere; Darkness;

DOI:10.1039/b902240f

Reference yield:

2,4-Dinitrofluorobenzene (70-34-8,65727-75-5) + 3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-β-D-glucopyranose (226382-59-8) → 2',4'-Dinitrophenyl 3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-β-D-glucopyranoside (111524-65-3) + 2',4'-Dinitrophenyl 3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-α-D-glucopyranoside (111524-64-2)

Guidance literature:

3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-β-D-glucopyranose; 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 1.5h; Further stages.;

DOI:10.1021/ja992044h

Reference yield:

2,4-Dinitrofluorobenzene (70-34-8,65727-75-5) + 3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-α-D-glucopyranosyl bromide (34245-85-7) → 2',4'-Dinitrophenyl 3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-β-D-glucopyranoside (111524-65-3) + 2',4'-Dinitrophenyl 3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-α-D-glucopyranoside (111524-64-2)

Guidance literature:

With 1,4-diaza-bicyclo[2.2.2]octane; Multistep reaction; 1.) hydrolysis;

DOI:10.1021/ja00258a047

upstream raw materials:

2,4-Dinitrofluorobenzene

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

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

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

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