N⁶-benzoyl-9-[3,5-O-(di-tert-butylsilylene)-2-deoxy-4-thio-β-D-ribofuranosyl]adenine

Base Information

• Chemical Name: N⁶-benzoyl-9-[3,5-O-(di-tert-butylsilylene)-2-deoxy-4-thio-β-D-ribofuranosyl]adenine
• CAS No.: 457653-18-8
• Molecular Formula: C₂₅H₃₃N₅O₃SSi
• Molecular Weight: 511.72

Synonyms:N⁶-benzoyl-9-[3,5-O-(di-tert-butylsilylene)-2-deoxy-4-thio-β-D-ribofuranosyl]adenine

Chemical Property of N⁶-benzoyl-9-[3,5-O-(di-tert-butylsilylene)-2-deoxy-4-thio-β-D-ribofuranosyl]adenine

Chemical Property:

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Technology Process of N⁶-benzoyl-9-[3,5-O-(di-tert-butylsilylene)-2-deoxy-4-thio-β-D-ribofuranosyl]adenine

There total 14 articles about N⁶-benzoyl-9-[3,5-O-(di-tert-butylsilylene)-2-deoxy-4-thio-β-D-ribofuranosyl]adenine 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: 65.0%

N6-benzoyl-9-[(2R)-3,5-O-(di-tert-butylsilylene)-2-deoxy-2-phenylseleno-4-thio-β-D-ribofuranosyl]adenine (457653-17-7) → N6-benzoyl-9-[3,5-O-(di-tert-butylsilylene)-2-deoxy-4-thio-β-D-ribofuranosyl]adenine (457653-18-8)

Guidance literature:

With triethyl borane; oxygen; tri-n-butyl-tin hydride; In tetrahydrofuran; benzene; at 20 ℃; for 1h;

DOI:10.1021/jo020037x

Reference yield:

(2R,3S)-5-(benzylthio)-2-(hydroxymethyl)tetrahydrothiophen-3-ol (134700-25-7) → N6-benzoyl-9-[3,5-O-(di-tert-butylsilylene)-2-deoxy-4-thio-β-D-ribofuranosyl]adenine (457653-18-8)

Guidance literature:

Multi-step reaction with 9 steps

1: 5.46 g / imidazole; DMF / 20 °C

2: acetic acid / 2 h / 20 °C

3: 670 mg / ammonia / methanol / 20 °C

4: 4-dimethylaminopyridine / CH₂Cl₂ / 0 °C

5: 113 mg / CH₂Cl₂ / 20 °C

6: tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / 0 °C

7: 30.9 mg / 4-(dimethylamino)pyridine; DMF / 0 °C

8: 6 percent / acetonitrile / 0 °C

9: 65 percent / tributyltin hydride; triethylborane; oxygen / benzene; tetrahydrofuran / 1 h / 20 °C

With 1H-imidazole; dmap; triethyl borane; tetrabutyl ammonium fluoride; ammonia; oxygen; tri-n-butyl-tin hydride; acetic acid; N,N-dimethyl-formamide; In tetrahydrofuran; methanol; dichloromethane; acetonitrile; benzene;

DOI:10.1021/jo020037x

Reference yield:

benzyl 3,5-di-O-benzyl-2-deoxy-1,4-dithio-D-erythro-pentofuranoside (134938-97-9) → N6-benzoyl-9-[3,5-O-(di-tert-butylsilylene)-2-deoxy-4-thio-β-D-ribofuranosyl]adenine (457653-18-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: boron tribromide; methanol; pyridine / CH₂Cl₂ / 0.5 h / -70 °C

2.1: 625 mg / imidazole / dimethylformamide / 20 °C

3.1: m-chloroperoxybenzoic acid / CH₂Cl₂ / 1.5 h / -70 °C

3.2: 57 percent / diisopropylethylamine / xylene / Heating

4.1: 6 percent / acetonitrile / 0 °C

5.1: 65 percent / tributyltin hydride; triethylborane; oxygen / benzene; tetrahydrofuran / 1 h / 20 °C

With pyridine; 1H-imidazole; methanol; triethyl borane; oxygen; tri-n-butyl-tin hydride; boron tribromide; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile; benzene;

DOI:10.1021/jo020037x

upstream raw materials:

N⁶-benzoyl-9-[(2R)-3,5-O-(di-tert-butylsilylene)-2-deoxy-2-phenylseleno-4-thio-β-D-ribofuranosyl]adenine

benzyl 3,5-di-O-benzyl-2-deoxy-1,4-dithio-D-erythro-pentofuranoside

bis(trimethylsilyl)-N⁶-benzoyladenine

(2R,3S)-5-(benzylthio)-2-(hydroxymethyl)tetrahydrothiophen-3-ol

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