Benzoic acid (2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-ethynyl-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl ester

Base Information

Chemical Name:Benzoic acid (2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-ethynyl-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl ester
CAS No.:197297-91-9
Molecular Formula:C₁₈H₁₆N₂O₇
Molecular Weight:372.334
Hs Code.:

Synonyms:Benzoic acid (2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-ethynyl-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl ester

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Chemical Property of Benzoic acid (2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-ethynyl-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl ester

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Technology Process of Benzoic acid (2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-ethynyl-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl ester

There total 4 articles about Benzoic acid (2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-ethynyl-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl ester 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%

: 197297-89-5
benzoic acid 4-(tert-butyl-dimethyl-silanyloxy)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-3-trimethylsilanylethynyl-tetrahydro-furan-2-ylmethyl ester

: 197297-91-9
Benzoic acid (2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-ethynyl-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl ester

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran;
DOI:10.1021/jo9704568

Reference yield:

: 90813-54-0
2',5'-bis-O-tert-butyldimethylsilyl-3'-ketouridine

: 197297-91-9
Benzoic acid (2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-ethynyl-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: CF₃COOH / H₂O / 0.5 h / 0 °C

2.1: BuLi / tetrahydrofuran; hexane / 1 h / -78 - -20 °C

2.2: CeCl₃ / tetrahydrofuran; hexane / 1 h / -78 °C

2.3: 0.74 g / tetrahydrofuran; hexane / 3 h / -78 °C

3.1: 83 percent / pyridine / -10 - 20 °C

4.1: 60 percent / Bu₄NF / tetrahydrofuran

With pyridine; n-butyllithium; tetrabutyl ammonium fluoride; trifluoroacetic acid; In tetrahydrofuran; hexane; water; 1.1: desilylation / 2.1: Metallation / 2.2: transmetallation / 2.3: Addition / 3.1: Esterification / 4.1: desilylation;
DOI:10.1021/jo9704568

Reference yield:

: 162611-11-2
1-[2-O-(tert-butyldimethylsilyl)-β-D-erythro-pentofuran-3-ulosyl]uracil

: 197297-91-9
Benzoic acid (2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-ethynyl-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: BuLi / tetrahydrofuran; hexane / 1 h / -78 - -20 °C

1.2: CeCl₃ / tetrahydrofuran; hexane / 1 h / -78 °C

1.3: 0.74 g / tetrahydrofuran; hexane / 3 h / -78 °C

2.1: 83 percent / pyridine / -10 - 20 °C

3.1: 60 percent / Bu₄NF / tetrahydrofuran

With pyridine; n-butyllithium; tetrabutyl ammonium fluoride; In tetrahydrofuran; hexane; 1.1: Metallation / 1.2: transmetallation / 1.3: Addition / 2.1: Esterification / 3.1: desilylation;
DOI:10.1021/jo9704568