1-(2,3-dideoxy-2-fluoro-α-L-glycero-pent-2-enofuranosyl)-N⁴-benzoylcytosine

Base Information

Chemical Name:1-(2,3-dideoxy-2-fluoro-α-L-glycero-pent-2-enofuranosyl)-N⁴-benzoylcytosine
CAS No.:221616-85-9
Molecular Formula:C₁₆H₁₄FN₃O₄
Molecular Weight:331.303
Hs Code.:

1-(2,3-dideoxy-2-fluoro-α-L-glycero-pent-2-enofuranosyl)-N<sup>4</sup>-benzoylcytosine

Synonyms:1-(2,3-dideoxy-2-fluoro-α-L-glycero-pent-2-enofuranosyl)-N⁴-benzoylcytosine

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Chemical Property of 1-(2,3-dideoxy-2-fluoro-α-L-glycero-pent-2-enofuranosyl)-N⁴-benzoylcytosine

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Technology Process of 1-(2,3-dideoxy-2-fluoro-α-L-glycero-pent-2-enofuranosyl)-N⁴-benzoylcytosine

There total 5 articles about 1-(2,3-dideoxy-2-fluoro-α-L-glycero-pent-2-enofuranosyl)-N⁴-benzoylcytosine 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: 69.0%

: 221616-77-9
1-<5-O-(tert-butyldimethylsilyl)-2,3-dideoxy-2-fluoro-α-L-glycero-pent-2-enofuranosyl>-N⁴-benzoylcytosine

: 221616-85-9
1-(2,3-dideoxy-2-fluoro-α-L-glycero-pent-2-enofuranosyl)-N⁴-benzoylcytosine

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 1h; Ambient temperature;
DOI:10.1021/jm980651u

Reference yield:

: 221616-69-9
(E)/(Z)-ethyl 3-<(R)-2,2-dimethyl-1,3-dioxolan-4-yl>-2-fluoroacrylate

: 221616-85-9
1-(2,3-dideoxy-2-fluoro-α-L-glycero-pent-2-enofuranosyl)-N⁴-benzoylcytosine

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) conc. HCl, 2.) imidazole / 1.) EtOH, RT, 2 h, 2.) CH₂Cl₂, RT, 4 h

2: DIBAL-H / CH₂Cl₂ / 2 h / -78 °C

3: Et₃N / CH₂Cl₂ / 2 h / Ambient temperature

4: 1.) hexamethyldisilazane, ammonium sulfate, 2.) TMSOTf / 1.) reflux, 3 h, 2.) CH₃CN, RT, 2 h

5: 69 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature

With 1H-imidazole; hydrogenchloride; ammonium sulfate; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jm980651u

Reference yield:

: 210474-50-3
1-acetyl-4-<(tert-butyldimethylsilyloxy)methyl>-2-fluoro-2-buten-4-olide

: 221616-85-9
1-(2,3-dideoxy-2-fluoro-α-L-glycero-pent-2-enofuranosyl)-N⁴-benzoylcytosine

Guidance literature:: Multi-step reaction with 2 steps

1: 1.) hexamethyldisilazane, ammonium sulfate, 2.) TMSOTf / 1.) reflux, 3 h, 2.) CH₃CN, RT, 2 h

2: 69 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature

With ammonium sulfate; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran;
DOI:10.1021/jm980651u