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

Base Information

• Chemical Name: 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
• CAS No.: 201673-42-9
• Molecular Formula: C₄₆H₅₁N₃O₇Si
• Molecular Weight: 786.012
• Mol file: 201673-42-9.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 8 articles about 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 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: 85.0%

benzoic acid anhydride (93-97-0) + 4-Amino-1-[(2S,4S,5R)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-5-prop-1-ynyl-1H-pyrimidin-2-one (201673-39-4) → 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)

Guidance literature:

In pyridine; for 43h;

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

Reference yield:

3',5'-di-O-(p-toluoyl)-5-iodo-α-2'-desoxyuridine (104267-95-0) → 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)

Guidance literature:

Multi-step reaction with 6 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

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

Guidance literature:

Multi-step reaction with 7 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

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

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

upstream raw materials:

benzoic acid anhydride

4-Amino-1-[(2S,4S,5R)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-5-prop-1-ynyl-1H-pyrimidin-2-one

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

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

Downstream raw materials:

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