1-[4-(tert-butyl-diphenyl-silanyloxymethyl)-cyclobut-2-enylmethyl]-5-methyl-1H-pyrimidine-2,4-dione

Base Information

• Chemical Name: 1-[4-(tert-butyl-diphenyl-silanyloxymethyl)-cyclobut-2-enylmethyl]-5-methyl-1H-pyrimidine-2,4-dione
• CAS No.: 446840-32-0
• Molecular Formula: C₂₇H₃₂N₂O₃Si
• Molecular Weight: 460.648
• Mol file: 446840-32-0.mol

Synonyms:1-[4-(tert-butyl-diphenyl-silanyloxymethyl)-cyclobut-2-enylmethyl]-5-methyl-1H-pyrimidine-2,4-dione

Chemical Property of 1-[4-(tert-butyl-diphenyl-silanyloxymethyl)-cyclobut-2-enylmethyl]-5-methyl-1H-pyrimidine-2,4-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[4-(tert-butyl-diphenyl-silanyloxymethyl)-cyclobut-2-enylmethyl]-5-methyl-1H-pyrimidine-2,4-dione

There total 7 articles about 1-[4-(tert-butyl-diphenyl-silanyloxymethyl)-cyclobut-2-enylmethyl]-5-methyl-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: 93.0%

3-benzoyl-1-[4-(tert-butyl-diphenyl-silanyloxymethyl)-cyclobut-2-enylmethyl]-5-methyl-1H-pyrimidine-2,4-dione (446840-31-9) → 1-[4-(tert-butyl-diphenyl-silanyloxymethyl)-cyclobut-2-enylmethyl]-5-methyl-1H-pyrimidine-2,4-dione (446840-32-0)

Guidance literature:

With ammonium hydroxide; In methanol; at 20 ℃; for 48h;

DOI:10.1016/j.tet.2005.05.096

Reference yield:

3-benzoyl-1-[4-(tert-butyl-diphenyl-silanyloxymethyl)-cyclobut-2-enylmethyl]-5-methyl-1H-pyrimidine-2,4-dione (446840-31-9) → 1-[4-(tert-butyl-diphenyl-silanyloxymethyl)-cyclobut-2-enylmethyl]-5-methyl-1H-pyrimidine-2,4-dione (446840-32-0) + 1-[4-(tert-butyl-diphenyl-silanyloxymethyl)-cyclobut-2-enylmethyl]-5-methyl-1H-pyrimidine-2,4-dione

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; at 20 ℃; for 72h; Title compound not separated from byproducts;

DOI:10.1016/S0040-4020(02)00323-X

Reference yield:

N-3-benzoylthymine (4330-20-5) → 1-[4-(tert-butyl-diphenyl-silanyloxymethyl)-cyclobut-2-enylmethyl]-5-methyl-1H-pyrimidine-2,4-dione (446840-32-0)

Guidance literature:

Multi-step reaction with 2 steps

1: triphenylphosphine; diethyl azodicarboxylate / tetrahydrofuran / 20 °C

2: aq. NaOH / dioxane / 72 h / 20 °C

With sodium hydroxide; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane; 1: Mitsunobu reaction;

DOI:10.1016/S0040-4020(02)00323-X

upstream raw materials:

3-benzoyl-1-[4-(tert-butyl-diphenyl-silanyloxymethyl)-cyclobut-2-enylmethyl]-5-methyl-1H-pyrimidine-2,4-dione

N-3-benzoylthymine

tert-butylchlorodiphenylsilane

(-)-[(1S,4R)-4-({[tert-butyl(diphenyl)silyl]oxy}methyl)cyclobut-2-enyl]methanol

Downstream raw materials:

(+)-N₁-[(1S,2R,3S)-2-(tert-butyl-diphenyl-silyloxymethyl)-3-hydroxy-cyclobutyl]methyl-5-methyl-1H,3H-pyrimidine-2,4-dione

(-)-N₁-[(1S,2R,4R)-2-(tert-butyl-diphenyl-silyloxymethyl)-4-hydroxy-cyclobutyl]methyl-5-methyl-1H,3H-pyrimidine-2,4-dione

(-)-N₁-[(1S,2S,3R,4R)-2,3-dihydroxy-4-(tert-butyl-diphenyl-silyloxymethyl)-cyclobutyl]methyl-5-methyl-1H,3H-pyrimidine-2,4-dione