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

Base Information

• Chemical Name: N₃-benzoyl-1-[(1R,4S)-4-[(tert-butyldiphenylsilyl)oxy]-2-cyclopenten-1-yl]thymine
• CAS No.: 239808-22-1
• Molecular Formula: C₃₃H₃₄N₂O₄Si
• Molecular Weight: 550.729

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

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

Chemical Property:

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

There total 5 articles about N₃-benzoyl-1-[(1R,4S)-4-[(tert-butyldiphenylsilyl)oxy]-2-cyclopenten-1-yl]thymine 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: 94.0%

N-3-benzoylthymine (4330-20-5) + (1R,4S)-4-[(tert-butyldiphenylsilyl)oxy]-1-(ethoxycarbonyloxy)-2-cyclopentene → N3-benzoyl-1-[(1R,4S)-4-[(tert-butyldiphenylsilyl)oxy]-2-cyclopenten-1-yl]thymine (239808-22-1)

Guidance literature:

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; triphenylphosphine; In tetrahydrofuran; at 20 ℃; for 0.5h;

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]thymine (239808-22-1)

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: 94 percent / Pd₂(dba)3*CHCl₃; PPh₃ / tetrahydrofuran / 0.5 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]thymine (239808-22-1)

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: 94 percent / Pd₂(dba)3*CHCl₃; PPh₃ / tetrahydrofuran / 0.5 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:

N-3-benzoylthymine

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

1-[(1R,4S)-4-[N-(tert-butyldiphenylsilyl)oxyamino]-2-cyclopenten-1-yl]thymine

N₃-benzoyl-1-[(1R,4S)-4-(N-benzyloxyamino)-2-cyclopenten-1-yl]thymine

N₃-benzoyl-1-[(1R,4S)-4-(ethoxycarbonyloxy)-2-cyclopenten-1-yl]thymine

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