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

Base Information

Chemical Name:9-(5-O-benzoyl-3-C-ethynyl-2-O-[m-(trifluoromethyl)benzoyl]-β-D-ribo-pentofuranosyl)adenine
CAS No.:197297-94-2
Molecular Formula:C₂₇H₂₀F₃N₅O₆
Molecular Weight:567.481
Hs Code.:

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

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

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

There total 5 articles about 9-(5-O-benzoyl-3-C-ethynyl-2-O-[m-(trifluoromethyl)benzoyl]-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: 90.0%

: 2251-65-2
3-(Trifluoromethyl)benzoyl chloride

: 197297-92-0
9-(5-O-benzoyl-3-C-ethynyl-β-D-ribo-pentofuranosyl)adenine

: 197297-94-2
9-(5-O-benzoyl-3-C-ethynyl-2-O-[m-(trifluoromethyl)benzoyl]-β-D-ribo-pentofuranosyl)adenine

Guidance literature:: With pyridine; dmap; at 0 - 20 ℃; for 3h;
DOI:10.1021/jo9704568

Reference yield:

: 124583-06-8
9-[2-O-(tert-butyldimethylsilyl)-β-D-erythro-pentofuran-3-ulosyl]adenine

: 197297-94-2
9-(5-O-benzoyl-3-C-ethynyl-2-O-[m-(trifluoromethyl)benzoyl]-β-D-ribo-pentofuranosyl)adenine

Guidance literature:: Multi-step reaction with 4 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

3.1: 96 percent / Bu₄NF / tetrahydrofuran / 0.5 h / 20 °C

4.1: 90 percent / DMAP; pyridine / 3 h / 0 - 20 °C

With pyridine; dmap; n-butyllithium; tetrabutyl ammonium fluoride; In tetrahydrofuran; hexane; 1.1: Metallation / 1.2: transmetallation / 1.3: Addition / 2.1: Esterification / 3.1: desilylation / 4.1: Esterification;
DOI:10.1021/jo9704568

Reference yield:

: 86734-95-4
9-(2,5-di-O-tert-butyldimethylsilyl-β-D-erythro-pentofuran-3-ulosyl)adenosine

: 197297-94-2
9-(5-O-benzoyl-3-C-ethynyl-2-O-[m-(trifluoromethyl)benzoyl]-β-D-ribo-pentofuranosyl)adenine

Guidance literature:: Multi-step reaction with 5 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

4.1: 96 percent / Bu₄NF / tetrahydrofuran / 0.5 h / 20 °C

5.1: 90 percent / DMAP; pyridine / 3 h / 0 - 20 °C

With pyridine; dmap; n-butyllithium; tetrabutyl ammonium fluoride; trifluoroacetic acid; In tetrahydrofuran; hexane; water; 1.1: desilylation / 2.1: Metallation / 2.2: transmetallation / 2.3: Addition / 3.1: Esterification / 4.1: desilylation / 5.1: Esterification;
DOI:10.1021/jo9704568