4-(1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)but-3-ynyl 4-methylbenzenesulfonate

Base Information

Chemical Name:4-(1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)but-3-ynyl 4-methylbenzenesulfonate
CAS No.:84559-05-7
Molecular Formula:C₂₀H₂₂N₂O₈S
Molecular Weight:450.469
Hs Code.:

Synonyms:4-(1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)but-3-ynyl 4-methylbenzenesulfonate

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Chemical Property of 4-(1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)but-3-ynyl 4-methylbenzenesulfonate

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Technology Process of 4-(1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)but-3-ynyl 4-methylbenzenesulfonate

There total 3 articles about 4-(1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)but-3-ynyl 4-methylbenzenesulfonate 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%

: 85267-66-9
5-<4-(p-Toluenesulfonyloxy)butynyl>-3',5'-di-O-p-toluyl-2'-deoxyuridine

: 84559-05-7
4-(1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)but-3-ynyl 4-methylbenzenesulfonate

Guidance literature:: With sodium methylate; In methanol; at 25 ℃; for 5h;
DOI:10.1021/jo00159a012

Reference yield:

: 31356-86-2
1-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]-5-iodouracil

: 84559-05-7
4-(1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)but-3-ynyl 4-methylbenzenesulfonate

Guidance literature:: Multi-step reaction with 4 steps

1: 85 percent / Et₃N / (Ph₃P)2PdCl₂, CuI / 4 h / 50 °C

2: 90 percent / CF₃COOH / CH₂Cl₂; methanol / 1.5 h / 25 °C

3: 65 percent / pyridine / 18 h / 25 °C

4: 60 percent / 0.1 N NaOMe / methanol / 5 h / 25 °C

With pyridine; sodium methylate; triethylamine; trifluoroacetic acid; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In methanol; dichloromethane;
DOI:10.1021/jo00159a012

Reference yield:

: 77875-94-6
C₃₄H₃₆N₂O₉

: 84559-05-7
4-(1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)but-3-ynyl 4-methylbenzenesulfonate

Guidance literature:: Multi-step reaction with 3 steps

1: 90 percent / CF₃COOH / CH₂Cl₂; methanol / 1.5 h / 25 °C

2: 65 percent / pyridine / 18 h / 25 °C

3: 60 percent / 0.1 N NaOMe / methanol / 5 h / 25 °C

With pyridine; sodium methylate; trifluoroacetic acid; In methanol; dichloromethane;
DOI:10.1021/jo00159a012