Technology Process of (2'R)-α-D-N4-benzoyl-5'-(tert-butyldimethylsilyl)-2',3'-dideoxy-2'-trifluoromethylcytidine
There total 6 articles about (2'R)-α-D-N4-benzoyl-5'-(tert-butyldimethylsilyl)-2',3'-dideoxy-2'-trifluoromethylcytidine which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
4-N-benzoylcytosine; (2R,4S)-1-O-acetyl-5-(tert-butyldimethylsilyl)-2,3-dideoxy-2-trifluoromethylpentofuranose;
With
N,O-bis-(trimethylsilyl)-acetamide;
In
acetonitrile;
for 0.5h;
Heating;
With
trimethylsilyl trifluoromethanesulfonate;
In
acetonitrile;
at 20 ℃;
for 24h;
Further stages.;
DOI:10.1021/jo005520r
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: 68 percent / CuI / dimethylformamide; hexamethylphosphoric acid triamide / 29 h / 75 °C
2.1: H2 / Pd/C / ethanol / 24 h / 20 °C / 760.05 Torr
2.2: 78 percent / HCl / H2O / 50 - 55 °C
3.1: 53 percent / imidazole / CH2Cl2 / 0.83 h / 20 °C
4.1: 64 percent / DIBAL-H / tetrahydrofuran; cyclohexane / 5 h / -78 °C
5.1: 93 percent / DMAP / CH2Cl2 / 20 °C
6.1: N,O-bis(trimethylsilyl)acetamide / acetonitrile / 0.5 h / Heating
6.2: 32 percent / TMSOTf / acetonitrile / 24 h / 20 °C
With
1H-imidazole; dmap; copper(l) iodide; N,O-bis-(trimethylsilyl)-acetamide; hydrogen; diisobutylaluminium hydride;
palladium on activated charcoal;
In
tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; dichloromethane; cyclohexane; N,N-dimethyl-formamide; acetonitrile;
1.1: Substitution / 2.1: Catalytic hydrogenation / 2.2: Substitution / 3.1: Substitution / 4.1: Reduction / 5.1: Acetylation / 6.1: Condensation / 6.2: Substitution;
DOI:10.1021/jo005520r
- Guidance literature:
-
Multi-step reaction with 5 steps
1.1: H2 / Pd/C / ethanol / 24 h / 20 °C / 760.05 Torr
1.2: 78 percent / HCl / H2O / 50 - 55 °C
2.1: 53 percent / imidazole / CH2Cl2 / 0.83 h / 20 °C
3.1: 64 percent / DIBAL-H / tetrahydrofuran; cyclohexane / 5 h / -78 °C
4.1: 93 percent / DMAP / CH2Cl2 / 20 °C
5.1: N,O-bis(trimethylsilyl)acetamide / acetonitrile / 0.5 h / Heating
5.2: 32 percent / TMSOTf / acetonitrile / 24 h / 20 °C
With
1H-imidazole; dmap; N,O-bis-(trimethylsilyl)-acetamide; hydrogen; diisobutylaluminium hydride;
palladium on activated charcoal;
In
tetrahydrofuran; ethanol; dichloromethane; cyclohexane; acetonitrile;
1.1: Catalytic hydrogenation / 1.2: Substitution / 2.1: Substitution / 3.1: Reduction / 4.1: Acetylation / 5.1: Condensation / 5.2: Substitution;
DOI:10.1021/jo005520r
