6-[2-(4-nitrophenyl)ethoxy]-3-(β-D-glycero-pentofuran-3'-ulos-1'-yl)-2-fluoropyridine

Base Information

• Chemical Name: 6-[2-(4-nitrophenyl)ethoxy]-3-(β-D-glycero-pentofuran-3'-ulos-1'-yl)-2-fluoropyridine
• CAS No.: 884660-53-1
• Molecular Formula: C₁₈H₁₇FN₂O₆
• Molecular Weight: 376.341
• Mol file: 884660-53-1.mol

Synonyms:6-[2-(4-nitrophenyl)ethoxy]-3-(β-D-glycero-pentofuran-3'-ulos-1'-yl)-2-fluoropyridine

Chemical Property of 6-[2-(4-nitrophenyl)ethoxy]-3-(β-D-glycero-pentofuran-3'-ulos-1'-yl)-2-fluoropyridine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-[2-(4-nitrophenyl)ethoxy]-3-(β-D-glycero-pentofuran-3'-ulos-1'-yl)-2-fluoropyridine

There total 8 articles about 6-[2-(4-nitrophenyl)ethoxy]-3-(β-D-glycero-pentofuran-3'-ulos-1'-yl)-2-fluoropyridine 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:

((2R,5R)-3-(tert-Butyl-diphenyl-silanyloxy)-5-{2-fluoro-6-[2-(4-nitro-phenyl)-ethoxy]-pyridin-3-yl}-2,5-dihydro-furan-2-yl)-methanol → 6-[2-(4-nitrophenyl)ethoxy]-3-(β-D-glycero-pentofuran-3'-ulos-1'-yl)-2-fluoropyridine (884660-53-1)

Guidance literature:

With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; methanol; at 0 ℃; for 0.5h;

DOI:10.1021/jo060066y

Reference yield:

2.6-diaminopyridine (141-86-6) → 6-[2-(4-nitrophenyl)ethoxy]-3-(β-D-glycero-pentofuran-3'-ulos-1'-yl)-2-fluoropyridine (884660-53-1)

Guidance literature:

Multi-step reaction with 8 steps

1: 60 percent / AcOH; H₂SO₄; I₂ / periodic acid / H₂O / 5 h / 55 °C

2: 85 percent / pyridine / 12 h / 20 °C

3: 64 percent / HBF₄; NaNO₂ / H₂O / 2 h / -5 °C

4: 88 percent / H₂SO₄ / methanol; H₂O / 12 h / 25 °C

5: H₂SO₄; NaNO₂ / H₂O / 2 h / -5 °C

6: 145 mg / Ph₃P; diethyl azodicarboxylate / dioxane / 2 h / 20 °C

7: tris(dibenzylideneacetone)palladium; tris(pentafluorophenyl)phosphine; N,N-diisopropylethylamine / acetonitrile / 48 h / 90 °C

8: 686 mg / (n-Bu)4NF; AcOH / tetrahydrofuran; methanol / 0.5 h / 0 °C

With pyridine; tetrafluoroboric acid; tris(dibenzylideneacetone)palladium; sulfuric acid; tetrabutyl ammonium fluoride; iodine; acetic acid; N-ethyl-N,N-diisopropylamine; triphenylphosphine; tris(pentafluorophenyl)phosphine; sodium nitrite; diethylazodicarboxylate; periodic acid; In tetrahydrofuran; 1,4-dioxane; methanol; water; acetonitrile; 7: Heck coupling;

DOI:10.1021/jo060066y

Reference yield:

6-amino-2-fluoro-3-iodopyridine (884660-47-3) → 6-[2-(4-nitrophenyl)ethoxy]-3-(β-D-glycero-pentofuran-3'-ulos-1'-yl)-2-fluoropyridine (884660-53-1)

Guidance literature:

Multi-step reaction with 4 steps

1: H₂SO₄; NaNO₂ / H₂O / 2 h / -5 °C

2: 145 mg / Ph₃P; diethyl azodicarboxylate / dioxane / 2 h / 20 °C

3: tris(dibenzylideneacetone)palladium; tris(pentafluorophenyl)phosphine; N,N-diisopropylethylamine / acetonitrile / 48 h / 90 °C

4: 686 mg / (n-Bu)4NF; AcOH / tetrahydrofuran; methanol / 0.5 h / 0 °C

With tris(dibenzylideneacetone)palladium; sulfuric acid; tetrabutyl ammonium fluoride; acetic acid; N-ethyl-N,N-diisopropylamine; triphenylphosphine; tris(pentafluorophenyl)phosphine; sodium nitrite; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane; methanol; water; acetonitrile; 3: Heck coupling;

DOI:10.1021/jo060066y

upstream raw materials:

2,6-diamino-3-iodopyridine

6-amino-2-fluoro-3-iodopyridine

2-fluoro-6-hydroxy-3-iodopyridine

N-(6-fluoro-5-iodopyridin-2-yl)acetamide

Downstream raw materials:

3-[2-deoxy-β-D-erythro-pentafuranosyl]-2-fluoro-6-[2-(4-nitrophenyl)ethoxy]pyridine