(2R,3R,4S,5R)-4-acetoxy-2-((R)-1-(benzoyloxy)ethyl)-5-cyano-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-yl benzoate

Base Information

Chemical Name:(2R,3R,4S,5R)-4-acetoxy-2-((R)-1-(benzoyloxy)ethyl)-5-cyano-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-yl benzoate
CAS No.:1402821-87-7
Molecular Formula:C₂₇H₂₃N₃O₉
Molecular Weight:533.494
Hs Code.:

Synonyms:(2R,3R,4S,5R)-4-acetoxy-2-((R)-1-(benzoyloxy)ethyl)-5-cyano-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-yl benzoate

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Chemical Property of (2R,3R,4S,5R)-4-acetoxy-2-((R)-1-(benzoyloxy)ethyl)-5-cyano-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-yl benzoate

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Technology Process of (2R,3R,4S,5R)-4-acetoxy-2-((R)-1-(benzoyloxy)ethyl)-5-cyano-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-yl benzoate

There total 8 articles about (2R,3R,4S,5R)-4-acetoxy-2-((R)-1-(benzoyloxy)ethyl)-5-cyano-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-yl benzoate 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%

: 1402821-85-5
(R)-1-((2R,3S,4S,5R)-3-(benzoyloxy)-5-cyano-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4-hydroxytetrahydrofuran-2-yl)ethyl benzoate

: 108-24-7
acetic anhydride

: 1402821-87-7
(2R,3R,4S,5R)-4-acetoxy-2-((R)-1-(benzoyloxy)ethyl)-5-cyano-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-yl benzoate

Guidance literature:: With pyridine; at 20 ℃; for 2h;
DOI:10.1080/15257770.2015.1075550

Reference yield:

: 1402821-77-5
(3R,4R,5R)-5-((R)-1-(benzoyloxy)ethyl)-2-bromo-2-cyanotetrahydrofuran-3,4-diyl dibenzoate

: 1402821-87-7
(2R,3R,4S,5R)-4-acetoxy-2-((R)-1-(benzoyloxy)ethyl)-5-cyano-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-yl benzoate

Guidance literature:: Multi-step reaction with 6 steps

1: silver trifluoromethanesulfonate / acetonitrile; 1,2-dichloro-ethane / 0.5 h / 135 °C / Inert atmosphere; microwave irradiation

2: pyridine; hydrazine hydrate; acetic acid / 40 h / 20 °C

3: pyridine / 8 h / 20 °C

4: triethylamine / acetonitrile / 2 h / 20 °C / Heating

5: hydrogenchloride / N,N-dimethyl-formamide; water / 0.5 h / 20 °C / Heating

6: pyridine / 2 h / 20 °C

With pyridine; hydrogenchloride; silver trifluoromethanesulfonate; hydrazine hydrate; acetic acid; triethylamine; In water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetonitrile;

Reference yield:

: 1402821-78-6
(2R,3R,4R,5R)-5-((R)-1-(benzoyloxy)ethyl)-2-cyano-2-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3,4-diyl dibenzoate

: 1402821-87-7
(2R,3R,4S,5R)-4-acetoxy-2-((R)-1-(benzoyloxy)ethyl)-5-cyano-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-yl benzoate

Guidance literature:: Multi-step reaction with 5 steps

1: pyridine; hydrazine hydrate; acetic acid / 40 h / 20 °C

2: pyridine / 8 h / 20 °C

3: triethylamine / acetonitrile / 2 h / 20 °C / Heating

4: hydrogenchloride / N,N-dimethyl-formamide; water / 0.5 h / 20 °C / Heating

5: pyridine / 2 h / 20 °C

With pyridine; hydrogenchloride; hydrazine hydrate; acetic acid; triethylamine; In water; N,N-dimethyl-formamide; acetonitrile;