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-pyrimidine-2,4-dione

Base Information

• Chemical Name: 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-pyrimidine-2,4-dione
• CAS No.: 201673-37-2
• Molecular Formula: C₃₉H₄₆N₂O₇Si
• Molecular Weight: 682.889
• Mol file: 201673-37-2.mol

Synonyms: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-pyrimidine-2,4-dione

Chemical Property of 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-pyrimidine-2,4-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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-pyrimidine-2,4-dione

There total 5 articles about 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-pyrimidine-2,4-dione 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: 88.0%

tert-butyldimethylsilyl chloride (18162-48-6) + 5'-O-(4,4'-dimethoxytrityl)-5-(propyn-1-yl)-α,2'-deoxyuridine (201673-35-0) → 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-pyrimidine-2,4-dione (201673-37-2)

Guidance literature:

With 1H-imidazole; In pyridine; for 48h; Ambient temperature;

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

Reference yield:

3',5'-di-O-(p-toluoyl)-5-iodo-α-2'-desoxyuridine (104267-95-0) → 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-pyrimidine-2,4-dione (201673-37-2)

Guidance literature:

Multi-step reaction with 4 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

With 1H-imidazole; copper(l) iodide; sodium methylate; triethylamine; 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) → 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-pyrimidine-2,4-dione (201673-37-2)

Guidance literature:

Multi-step reaction with 5 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

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

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

upstream raw materials:

tert-butyldimethylsilyl chloride

5'-O-(4,4'-dimethoxytrityl)-5-(propyn-1-yl)-α,2'-deoxyuridine

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:

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

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

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