2',3'-isopropylidene-5'-(5-hydroxy-1-phenyl-1-pentyn-3-yl)-5'-deoxyadenosine

Base Information

Chemical Name:2',3'-isopropylidene-5'-(5-hydroxy-1-phenyl-1-pentyn-3-yl)-5'-deoxyadenosine
CAS No.:126616-56-6
Molecular Formula:C₂₄H₂₇N₅O₄
Molecular Weight:449.509
Hs Code.:

Synonyms:2',3'-isopropylidene-5'-(5-hydroxy-1-phenyl-1-pentyn-3-yl)-5'-deoxyadenosine

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Chemical Property of 2',3'-isopropylidene-5'-(5-hydroxy-1-phenyl-1-pentyn-3-yl)-5'-deoxyadenosine

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Technology Process of 2',3'-isopropylidene-5'-(5-hydroxy-1-phenyl-1-pentyn-3-yl)-5'-deoxyadenosine

There total 6 articles about 2',3'-isopropylidene-5'-(5-hydroxy-1-phenyl-1-pentyn-3-yl)-5'-deoxyadenosine 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: 97.0%

: 126616-55-5
2',3'-isopropylidene-5'-(5-((tert-butyldiphenylsilyl)oxy)-1-phenyl-1-pentyn-3-yl)-5'-deoxyadenosine

: 126616-56-6
2',3'-isopropylidene-5'-(5-hydroxy-1-phenyl-1-pentyn-3-yl)-5'-deoxyadenosine

Guidance literature:: With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; for 8.66667h; Ambient temperature;
DOI:10.1021/jo00297a034

Reference yield:

: 126616-46-4
N⁶-benzoyl-2',3'-isopropylidene-5'-(2-hydroxytetrahydrofuran-3-yl)-5'-deoxyadenosine

: 126616-56-6
2',3'-isopropylidene-5'-(5-hydroxy-1-phenyl-1-pentyn-3-yl)-5'-deoxyadenosine

Guidance literature:: Multi-step reaction with 5 steps

1: 39 percent / imidazole / dimethylformamide; hexamethylphosphoric acid triamide / 1.33 h / 50 °C

2: 31 percent / potassium tert-butoxide / tetrahydrofuran / -78 °C / a) 15 min b) 5 h

3: 78 percent / CuI, Et₃N / PdCl₂(PPh₃)2 / a) 50 deg C, 3 h b) room temp., overnight

4: 94 percent / NH₄OH / methanol / 18 h / Ambient temperature

5: 97 percent / HOAc, tetrabutylammonium fluoride / tetrahydrofuran / 8.67 h / Ambient temperature

With 1H-imidazole; ammonium hydroxide; copper(l) iodide; potassium tert-butylate; tetrabutyl ammonium fluoride; acetic acid; triethylamine; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; N,N-dimethyl-formamide;
DOI:10.1021/jo00297a034

Reference yield:

: 85681-04-5
N⁶-Benzoyl-2',3'-O-isopropylidene-5'-C-(2-oxotetrahydro-3-furanyl)-5'-deoxyadenosine

: 126616-56-6
2',3'-isopropylidene-5'-(5-hydroxy-1-phenyl-1-pentyn-3-yl)-5'-deoxyadenosine

Guidance literature:: Multi-step reaction with 6 steps

1: 74 percent / DIBAL / tetrahydrofuran; toluene / 3 h / -78 °C

2: 39 percent / imidazole / dimethylformamide; hexamethylphosphoric acid triamide / 1.33 h / 50 °C

3: 31 percent / potassium tert-butoxide / tetrahydrofuran / -78 °C / a) 15 min b) 5 h

4: 78 percent / CuI, Et₃N / PdCl₂(PPh₃)2 / a) 50 deg C, 3 h b) room temp., overnight

5: 94 percent / NH₄OH / methanol / 18 h / Ambient temperature

6: 97 percent / HOAc, tetrabutylammonium fluoride / tetrahydrofuran / 8.67 h / Ambient temperature

With 1H-imidazole; ammonium hydroxide; copper(l) iodide; potassium tert-butylate; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; acetic acid; triethylamine; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo00297a034