(2R,3R,4R,5R)-2-(4-amino-2-oxopyrimidin-1(2H)-yl)-5-((R)-1-(benzoyloxy)ethyl)-2-cyanotetrahydrofuran-3,4-diyl dibenzoate

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Chemical Name:(2R,3R,4R,5R)-2-(4-amino-2-oxopyrimidin-1(2H)-yl)-5-((R)-1-(benzoyloxy)ethyl)-2-cyanotetrahydrofuran-3,4-diyl dibenzoate
CAS No.:1402821-80-0
Molecular Formula:C₃₂H₂₆N₄O₈
Molecular Weight:594.58
Hs Code.:

Synonyms:(2R,3R,4R,5R)-2-(4-amino-2-oxopyrimidin-1(2H)-yl)-5-((R)-1-(benzoyloxy)ethyl)-2-cyanotetrahydrofuran-3,4-diyl dibenzoate

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Chemical Property of (2R,3R,4R,5R)-2-(4-amino-2-oxopyrimidin-1(2H)-yl)-5-((R)-1-(benzoyloxy)ethyl)-2-cyanotetrahydrofuran-3,4-diyl dibenzoate

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Technology Process of (2R,3R,4R,5R)-2-(4-amino-2-oxopyrimidin-1(2H)-yl)-5-((R)-1-(benzoyloxy)ethyl)-2-cyanotetrahydrofuran-3,4-diyl dibenzoate

There total 4 articles about (2R,3R,4R,5R)-2-(4-amino-2-oxopyrimidin-1(2H)-yl)-5-((R)-1-(benzoyloxy)ethyl)-2-cyanotetrahydrofuran-3,4-diyl dibenzoate 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: 60.0%

: 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

: 1402821-80-0
(2R,3R,4R,5R)-2-(4-amino-2-oxopyrimidin-1(2H)-yl)-5-((R)-1-(benzoyloxy)ethyl)-2-cyanotetrahydrofuran-3,4-diyl dibenzoate

Guidance literature:: (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; With dmap; 2,4,6-triisopropylphenylsulfonyl chloride; triethylamine; In acetonitrile; at 20 ℃; for 0.5h;

With ammonium hydroxide; In water; acetonitrile; for 0.25h;

Reference yield:

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

: 1402821-80-0
(2R,3R,4R,5R)-2-(4-amino-2-oxopyrimidin-1(2H)-yl)-5-((R)-1-(benzoyloxy)ethyl)-2-cyanotetrahydrofuran-3,4-diyl dibenzoate

Guidance literature:: Multi-step reaction with 2 steps

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

2.1: dmap; triethylamine; 2,4,6-triisopropylphenylsulfonyl chloride / acetonitrile / 0.5 h / 20 °C

2.2: 0.25 h

With dmap; 2,4,6-triisopropylphenylsulfonyl chloride; silver trifluoromethanesulfonate; triethylamine; In 1,2-dichloro-ethane; acetonitrile;

Reference yield:

: 72159-45-6
1-O-Acetyl-2,3,5-tri-O-benzoyl-6-deoxy-β-D-allofuranose

: 1402821-80-0
(2R,3R,4R,5R)-2-(4-amino-2-oxopyrimidin-1(2H)-yl)-5-((R)-1-(benzoyloxy)ethyl)-2-cyanotetrahydrofuran-3,4-diyl dibenzoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: boron trifluoride diethyl etherate / nitromethane / 0.75 h / 20 °C

2.1: N-Bromosuccinimide / tetrachloromethane / 5 h / 75 °C / UV-irradiation

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

4.1: triethylamine; 2,4,6-triisopropylphenylsulfonyl chloride; dmap / acetonitrile / 0.5 h / 20 °C

4.2: 0.25 h

With dmap; N-Bromosuccinimide; 2,4,6-triisopropylphenylsulfonyl chloride; boron trifluoride diethyl etherate; silver trifluoromethanesulfonate; triethylamine; In tetrachloromethane; nitromethane; 1,2-dichloro-ethane; acetonitrile;
DOI:10.1080/15257770.2015.1075550