9-[5-O-benzoyl-2-O-(tert-butyldimethylsilyl)-3-C-[(trimethylsilyl)ethynyl]-β-D-ribo-pentofuranosyl]adenine

Base Information

• Chemical Name: 9-[5-O-benzoyl-2-O-(tert-butyldimethylsilyl)-3-C-[(trimethylsilyl)ethynyl]-β-D-ribo-pentofuranosyl]adenine
• CAS No.: 197297-90-8
• Molecular Formula: C₂₈H₃₉N₅O₅Si₂
• Molecular Weight: 581.819
• Mol file: 197297-90-8.mol

Synonyms:9-[5-O-benzoyl-2-O-(tert-butyldimethylsilyl)-3-C-[(trimethylsilyl)ethynyl]-β-D-ribo-pentofuranosyl]adenine

Chemical Property of 9-[5-O-benzoyl-2-O-(tert-butyldimethylsilyl)-3-C-[(trimethylsilyl)ethynyl]-β-D-ribo-pentofuranosyl]adenine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 9-[5-O-benzoyl-2-O-(tert-butyldimethylsilyl)-3-C-[(trimethylsilyl)ethynyl]-β-D-ribo-pentofuranosyl]adenine

There total 3 articles about 9-[5-O-benzoyl-2-O-(tert-butyldimethylsilyl)-3-C-[(trimethylsilyl)ethynyl]-β-D-ribo-pentofuranosyl]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: 86.0%

benzoyl chloride (98-88-4) + 9-[2-O-(tert-butyldimethylsilyl)-3-C-[(trimethylsilyl)ethynyl]-β-D-ribo-pentofuranosyl]adenine (162611-19-0) → 9-[5-O-benzoyl-2-O-(tert-butyldimethylsilyl)-3-C-[(trimethylsilyl)ethynyl]-β-D-ribo-pentofuranosyl]adenine (197297-90-8)

Guidance literature:

With pyridine; at -10 - 20 ℃;

DOI:10.1021/jo9704568

Reference yield:

9-[2-O-(tert-butyldimethylsilyl)-β-D-erythro-pentofuran-3-ulosyl]adenine (124583-06-8) → 9-[5-O-benzoyl-2-O-(tert-butyldimethylsilyl)-3-C-[(trimethylsilyl)ethynyl]-β-D-ribo-pentofuranosyl]adenine (197297-90-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: BuLi / tetrahydrofuran; hexane / 1 h / -78 - -20 °C

1.2: CeCl₃ / tetrahydrofuran; hexane / 1 h / -78 °C

1.3: tetrahydrofuran; hexane / 3 h / -78 °C

2.1: 86 percent / pyridine / -10 - 20 °C

With pyridine; n-butyllithium; In tetrahydrofuran; hexane; 1.1: Metallation / 1.2: transmetallation / 1.3: Addition / 2.1: Esterification;

DOI:10.1021/jo9704568

Reference yield:

9-(2,5-di-O-tert-butyldimethylsilyl-β-D-erythro-pentofuran-3-ulosyl)adenosine (86734-95-4) → 9-[5-O-benzoyl-2-O-(tert-butyldimethylsilyl)-3-C-[(trimethylsilyl)ethynyl]-β-D-ribo-pentofuranosyl]adenine (197297-90-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: CF₃COOH / H₂O / 0.5 h / 0 °C

2.1: BuLi / tetrahydrofuran; hexane / 1 h / -78 - -20 °C

2.2: CeCl₃ / tetrahydrofuran; hexane / 1 h / -78 °C

2.3: tetrahydrofuran; hexane / 3 h / -78 °C

3.1: 86 percent / pyridine / -10 - 20 °C

With pyridine; n-butyllithium; trifluoroacetic acid; In tetrahydrofuran; hexane; water; 1.1: desilylation / 2.1: Metallation / 2.2: transmetallation / 2.3: Addition / 3.1: Esterification;

DOI:10.1021/jo9704568

upstream raw materials:

benzoyl chloride

9-[2-O-(tert-butyldimethylsilyl)-3-C-[(trimethylsilyl)ethynyl]-β-D-ribo-pentofuranosyl]adenine

9-[2-O-(tert-butyldimethylsilyl)-β-D-erythro-pentofuran-3-ulosyl]adenine

9-(2,5-di-O-tert-butyldimethylsilyl-β-D-erythro-pentofuran-3-ulosyl)adenosine

Downstream raw materials:

9-(5-O-benzoyl-3-C-ethynyl-β-D-ribo-pentofuranosyl)adenine

9-(5-O-benzoyl-3-C-ethynyl-2-O-[m-(trifluoromethyl)benzoyl]-β-D-ribo-pentofuranosyl)adenine