2-[2-(4-nitrophenyl)ethoxy]-5-[5'-O-(4,4'-dimethoxytrityl)-1',2'-dideoxy-β-D-erythro-pentafuranozyl]-3-methylpyridine

Base Information

Chemical Name:2-[2-(4-nitrophenyl)ethoxy]-5-[5'-O-(4,4'-dimethoxytrityl)-1',2'-dideoxy-β-D-erythro-pentafuranozyl]-3-methylpyridine
CAS No.:289681-53-4
Molecular Formula:C₄₀H₄₀N₂O₈
Molecular Weight:676.766
Hs Code.:

Synonyms:2-[2-(4-nitrophenyl)ethoxy]-5-[5'-O-(4,4'-dimethoxytrityl)-1',2'-dideoxy-β-D-erythro-pentafuranozyl]-3-methylpyridine

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Chemical Property of 2-[2-(4-nitrophenyl)ethoxy]-5-[5'-O-(4,4'-dimethoxytrityl)-1',2'-dideoxy-β-D-erythro-pentafuranozyl]-3-methylpyridine

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Technology Process of 2-[2-(4-nitrophenyl)ethoxy]-5-[5'-O-(4,4'-dimethoxytrityl)-1',2'-dideoxy-β-D-erythro-pentafuranozyl]-3-methylpyridine

There total 12 articles about 2-[2-(4-nitrophenyl)ethoxy]-5-[5'-O-(4,4'-dimethoxytrityl)-1',2'-dideoxy-β-D-erythro-pentafuranozyl]-3-methylpyridine 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: 62.0%

: 40615-36-9
4,4'-dimethoxytrityl chloride

: 289681-52-3
2-[2-(4-nitrophenyl)ethoxy]-5-(1',2'-dideoxy-β-D-erythro-pentofuranosyl)-3-methylpyridine

: 289681-53-4
2-[2-(4-nitrophenyl)ethoxy]-5-[5'-O-(4,4'-dimethoxytrityl)-1',2'-dideoxy-β-D-erythro-pentafuranozyl]-3-methylpyridine

Guidance literature:: With dmap; triethylamine; In pyridine; at 20 ℃; for 48h;
DOI:10.1006/bioo.2001.1209

Reference yield:

: 1603-40-3
3-methylpyridin-2-ylamine

: 289681-53-4
2-[2-(4-nitrophenyl)ethoxy]-5-[5'-O-(4,4'-dimethoxytrityl)-1',2'-dideoxy-β-D-erythro-pentafuranozyl]-3-methylpyridine

Guidance literature:: Multi-step reaction with 7 steps

1.1: 73 percent / HIO₄*2H₂O; I₂ / acetic acid; H₂O; H₂SO₄ / 4 h / 80 °C

2.1: NaNO₂; conc. H₂SO₄ / 0.25 h / 60 °C

2.2: 75 percent / H₃BO₃ / H₂O / 0 - 100 °C

3.1: 71 percent / P(C₆H₅)3; diethyl azodicarboxylate / dioxane / 1.5 h / 20 °C

4.1: 73 percent / bis(dibenzylideneacetone) palladium⁽⁰⁾; 1,3-bis(diphenylphosphino)propane; tri-n-butylamine / acetonitrile / 8 h / 80 °C

5.1: 80 percent / CH₃COOH; tetra-n-butylammonium fluoride / tetrahydrofuran / 0.17 h / 0 °C

6.1: 77 percent / sodium triacetoxyborohydride / acetonitrile; acetic acid / 0.17 h / 0 °C

7.1: 62 percent / dimethylaminopyridine; triethylamine / pyridine / 48 h / 20 °C

With dmap; tributyl-amine; sulfuric acid; 1,3-bis-(diphenylphosphino)propane; tetrabutyl ammonium fluoride; iodine; sodium tris(acetoxy)borohydride; acetic acid; periodic acid; triethylamine; triphenylphosphine; bis(dibenzylideneacetone)-palladium⁽⁰⁾; sodium nitrite; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane; pyridine; sulfuric acid; water; acetic acid; acetonitrile;
DOI:10.1006/bioo.2001.1209

Reference yield:

: 83467-48-5
1-[(2R,4S,5R)-4-(tert-butyldiphenylsilanyloxy)-5-hydroxymethyltetrahydrofuran-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

: 289681-53-4
2-[2-(4-nitrophenyl)ethoxy]-5-[5'-O-(4,4'-dimethoxytrityl)-1',2'-dideoxy-β-D-erythro-pentafuranozyl]-3-methylpyridine

Guidance literature:: Multi-step reaction with 5 steps

1.1: (NH₄)2SO₄; 1,1,1,3,3,3-hexamethyldisilazane / 2 h / Heating

1.2: 70 percent / K₂CO₃ / methanol / 0.5 h / 0 - 5 °C

2.1: 73 percent / bis(dibenzylideneacetone) palladium⁽⁰⁾; 1,3-bis(diphenylphosphino)propane; tri-n-butylamine / acetonitrile / 8 h / 80 °C

3.1: 80 percent / CH₃COOH; tetra-n-butylammonium fluoride / tetrahydrofuran / 0.17 h / 0 °C

4.1: 77 percent / sodium triacetoxyborohydride / acetonitrile; acetic acid / 0.17 h / 0 °C

5.1: 62 percent / dimethylaminopyridine; triethylamine / pyridine / 48 h / 20 °C

With dmap; ammonium sulfate; tributyl-amine; 1,3-bis-(diphenylphosphino)propane; tetrabutyl ammonium fluoride; sodium tris(acetoxy)borohydride; acetic acid; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In tetrahydrofuran; pyridine; acetic acid; acetonitrile;
DOI:10.1006/bioo.2001.1209