5'-O-(4,4'-dimethoxytrityl)-N-4-benzoyl-5-(propyn-1-yl)-α,2'-deoxycytidine

Base Information

• Chemical Name: 5'-O-(4,4'-dimethoxytrityl)-N-4-benzoyl-5-(propyn-1-yl)-α,2'-deoxycytidine
• CAS No.: 201673-44-1
• Molecular Formula: C₄₀H₃₇N₃O₇
• Molecular Weight: 671.75
• Mol file: 201673-44-1.mol

Synonyms:5'-O-(4,4'-dimethoxytrityl)-N-4-benzoyl-5-(propyn-1-yl)-α,2'-deoxycytidine

Chemical Property of 5'-O-(4,4'-dimethoxytrityl)-N-4-benzoyl-5-(propyn-1-yl)-α,2'-deoxycytidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5'-O-(4,4'-dimethoxytrityl)-N-4-benzoyl-5-(propyn-1-yl)-α,2'-deoxycytidine

There total 8 articles about 5'-O-(4,4'-dimethoxytrityl)-N-4-benzoyl-5-(propyn-1-yl)-α,2'-deoxycytidine 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: 78.0%

N-{1-[(2S,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-2-oxo-5-prop-1-ynyl-1,2-dihydro-pyrimidin-4-yl}-benzamide (201673-42-9) → 5'-O-(4,4'-dimethoxytrityl)-N-4-benzoyl-5-(propyn-1-yl)-α,2'-deoxycytidine (201673-44-1)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 5h;

DOI:10.1016/S0040-4020(97)10257-5

Reference yield:

3',5'-di-O-(p-toluoyl)-5-iodo-α-2'-desoxyuridine (104267-95-0) → 5'-O-(4,4'-dimethoxytrityl)-N-4-benzoyl-5-(propyn-1-yl)-α,2'-deoxycytidine (201673-44-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 6.35 g / CH₃ONa / methanol / 0.75 h / 22 °C

2: 1) CuI, 2) Et₃N / 1) (Ph₃P)4Pd / 1) 1.5 h, 2) 22 h

3: 83 percent / pyridine / 24 h

4: 88 percent / imidazole / pyridine / 48 h / Ambient temperature

5: 1) 1,2,4-triazole, POCl₃, 2) NH₄OH / 1) pyridine, room temperature, overnight, 2) dioxane, H₂O, 1 h

6: 85 percent / pyridine / 43 h

7: 78 percent / tetrabutylammonium fluoride / tetrahydrofuran / 5 h

With 1H-imidazole; 1,2,4-Triazole; ammonium hydroxide; copper(l) iodide; tetrabutyl ammonium fluoride; sodium methylate; triethylamine; trichlorophosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; pyridine; methanol;

DOI:10.1016/S0040-4020(97)10257-5

Reference yield:

2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride (4330-21-6) → 5'-O-(4,4'-dimethoxytrityl)-N-4-benzoyl-5-(propyn-1-yl)-α,2'-deoxycytidine (201673-44-1)

Guidance literature:

Multi-step reaction with 8 steps

1: p-nitrophenol, pyridine / CH₂Cl₂ / 20 h

2: 6.35 g / CH₃ONa / methanol / 0.75 h / 22 °C

3: 1) CuI, 2) Et₃N / 1) (Ph₃P)4Pd / 1) 1.5 h, 2) 22 h

4: 83 percent / pyridine / 24 h

5: 88 percent / imidazole / pyridine / 48 h / Ambient temperature

6: 1) 1,2,4-triazole, POCl₃, 2) NH₄OH / 1) pyridine, room temperature, overnight, 2) dioxane, H₂O, 1 h

7: 85 percent / pyridine / 43 h

8: 78 percent / tetrabutylammonium fluoride / tetrahydrofuran / 5 h

With pyridine; 1H-imidazole; 1,2,4-Triazole; ammonium hydroxide; copper(l) iodide; 4-nitro-phenol; tetrabutyl ammonium fluoride; sodium methylate; triethylamine; trichlorophosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; pyridine; methanol; dichloromethane;

DOI:10.1016/S0040-4020(97)10257-5

upstream raw materials:

N-{1-[(2S,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-2-oxo-5-prop-1-ynyl-1,2-dihydro-pyrimidin-4-yl}-benzamide

3',5'-di-O-(p-toluoyl)-5-iodo-α-2'-desoxyuridine

2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride

5-iodo-α-2'-desoxyuridine