(2R,3S,4S,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-2-((benzoyloxy)methyl)-5-cyano-4-hydroxytetrahydrofuran-3-yl benzoate

Base Information

Chemical Name:(2R,3S,4S,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-2-((benzoyloxy)methyl)-5-cyano-4-hydroxytetrahydrofuran-3-yl benzoate
CAS No.:167023-24-7
Molecular Formula:C₂₄H₂₀N₄O₇
Molecular Weight:476.445
Hs Code.:

Synonyms:(2R,3S,4S,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-2-((benzoyloxy)methyl)-5-cyano-4-hydroxytetrahydrofuran-3-yl benzoate

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Chemical Property of (2R,3S,4S,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-2-((benzoyloxy)methyl)-5-cyano-4-hydroxytetrahydrofuran-3-yl benzoate

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Technology Process of (2R,3S,4S,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-2-((benzoyloxy)methyl)-5-cyano-4-hydroxytetrahydrofuran-3-yl benzoate

There total 11 articles about (2R,3S,4S,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-2-((benzoyloxy)methyl)-5-cyano-4-hydroxytetrahydrofuran-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: 57.0%

: 167023-23-6
(2R,3R,4S,5R)-4-acetoxy-2-((benzoyloxy)methyl)-5-cyano-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-yl benzoate

: 167023-24-7
(2R,3S,4S,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-2-((benzoyloxy)methyl)-5-cyano-4-hydroxytetrahydrofuran-3-yl benzoate

Guidance literature:: (2R,3R,4S,5R)-4-acetoxy-2-((benzoyloxy)methyl)-5-cyano-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-yl benzoate; With dmap; 2,4,6-triisopropylphenylsulfonyl chloride; triethylamine; In acetonitrile; at 25 ℃; for 2h;

With ammonium hydroxide; In water; acetonitrile; at 25 ℃; for 2h;

Reference yield:

: 153959-67-2
1'-cyano-2'-deoxy-2'β-bromouridine

: 167023-24-7
(2R,3S,4S,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-2-((benzoyloxy)methyl)-5-cyano-4-hydroxytetrahydrofuran-3-yl benzoate

Guidance literature:: Multi-step reaction with 6 steps

1: 44 percent / TBAF / tetrahydrofuran / 12 h / Ambient temperature

2: 71 percent / pyridine / 2 h / Ambient temperature

3: 76 percent / aq. HCl / dimethylformamide / 48 h / Ambient temperature

4: 80 percent / DMAP / pyridine / 2 h / Ambient temperature

5: 85 percent / SOCl₂ / dimethylformamide / 2 h / Ambient temperature

With hydrogenchloride; dmap; thionyl chloride; tetrabutyl ammonium fluoride; In tetrahydrofuran; pyridine; N,N-dimethyl-formamide;
DOI:10.1080/07328319608002386

Reference yield:

: 167023-21-4
3',5'-di-O-benzoyl-1'-C-carbamoyl-O²,2'-cyclouridine

: 167023-24-7
(2R,3S,4S,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-2-((benzoyloxy)methyl)-5-cyano-4-hydroxytetrahydrofuran-3-yl benzoate

Guidance literature:: Multi-step reaction with 4 steps

1: 76 percent / aq. HCl / dimethylformamide / 48 h / Ambient temperature

2: 80 percent / DMAP / pyridine / 2 h / Ambient temperature

3: 85 percent / SOCl₂ / dimethylformamide / 2 h / Ambient temperature

With hydrogenchloride; dmap; thionyl chloride; In pyridine; N,N-dimethyl-formamide;
DOI:10.1080/07328319608002386