N₃-benzoyl-1-[(1R,4S)-4-[(tert-butyldiphenylsilyl)oxy]-2-cyclopenten-1-yl]uracil

Base Information

• Chemical Name: N₃-benzoyl-1-[(1R,4S)-4-[(tert-butyldiphenylsilyl)oxy]-2-cyclopenten-1-yl]uracil
• CAS No.: 239808-23-2
• Molecular Formula: C₃₂H₃₂N₂O₄Si
• Molecular Weight: 536.703

Synonyms:N₃-benzoyl-1-[(1R,4S)-4-[(tert-butyldiphenylsilyl)oxy]-2-cyclopenten-1-yl]uracil

Chemical Property of N₃-benzoyl-1-[(1R,4S)-4-[(tert-butyldiphenylsilyl)oxy]-2-cyclopenten-1-yl]uracil

Chemical Property:

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Technology Process of N₃-benzoyl-1-[(1R,4S)-4-[(tert-butyldiphenylsilyl)oxy]-2-cyclopenten-1-yl]uracil

There total 5 articles about N₃-benzoyl-1-[(1R,4S)-4-[(tert-butyldiphenylsilyl)oxy]-2-cyclopenten-1-yl]uracil 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: 95.0%

3-N-benzoyluracil (2775-87-3) + (1R,4S)-4-[(tert-butyldiphenylsilyl)oxy]-1-(ethoxycarbonyloxy)-2-cyclopentene → N3-benzoyl-1-[(1R,4S)-4-[(tert-butyldiphenylsilyl)oxy]-2-cyclopenten-1-yl]uracil (239808-23-2)

Guidance literature:

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; triphenylphosphine; In tetrahydrofuran; at 20 ℃; for 3h;

DOI:10.1248/cpb.47.1000

Reference yield:

meso-cis-1,4-diacetoxy-2-cyclopentene (60389-71-1,60410-14-2,61826-75-3) → N3-benzoyl-1-[(1R,4S)-4-[(tert-butyldiphenylsilyl)oxy]-2-cyclopenten-1-yl]uracil (239808-23-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 34 percent / porcine liver esterase; phosphate buffer / 48 h / 37 °C / pH 7.0

2: imidazole / dimethylformamide / 24 h / 0 °C

3: 28 percent NaOMe / methanol / 24 h / 20 °C

4: 97 percent / pyridine / 1.5 h / 20 °C

5: 95 percent / Pd₂(dba)3*CHCl₃; PPh₃ / tetrahydrofuran / 3 h / 20 °C

With pyridine; 1H-imidazole; porcine liver esterase; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; phosphate buffer; sodium methylate; triphenylphosphine; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; 1: Hydrolysis / 2: Substitution / 3: Deacetylation / 4: Substitution / 5: Substitution;

DOI:10.1248/cpb.47.1000

Reference yield:

(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate (60410-16-4) → N3-benzoyl-1-[(1R,4S)-4-[(tert-butyldiphenylsilyl)oxy]-2-cyclopenten-1-yl]uracil (239808-23-2)

Guidance literature:

Multi-step reaction with 4 steps

1: imidazole / dimethylformamide / 24 h / 0 °C

2: 28 percent NaOMe / methanol / 24 h / 20 °C

3: 97 percent / pyridine / 1.5 h / 20 °C

4: 95 percent / Pd₂(dba)3*CHCl₃; PPh₃ / tetrahydrofuran / 3 h / 20 °C

With pyridine; 1H-imidazole; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium methylate; triphenylphosphine; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; 1: Substitution / 2: Deacetylation / 3: Substitution / 4: Substitution;

DOI:10.1248/cpb.47.1000

upstream raw materials:

3-N-benzoyluracil

meso-cis-1,4-diacetoxy-2-cyclopentene

(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate

(1R,4S)-4-(t-butyldiphenylsilanyloxy)cyclopent-2-enol

Downstream raw materials:

1-[(1R,2S,3R,4S)-2,3-bis[(tert-butyldimethylsilyl)oxy]-4-[N-(tert-butyldiphenylsilyl)oxyamino]cyclopent-1-yl]uracil

1-[(1R,2S,3R,4S)-2,3-bis[(tert-butyldimethylsilyl)oxy]-4-[N-(tert-butyldiphenylsilyl)oxyamino]cyclopent-1-yl]cytosine

1-[(1R,2S,3R,4S)-4-[N-(tert-butyldiphenylsilyl)oxyamino]-2,3-dihydroxycyclopent-1-yl]uracil

1-[(1S,4R)-4-[N-(tert-butyldiphenylsilyl)oxyamino]cyclopent-1-yl]uracil

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