(2R,3R,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(phenylselenenyl)tetrahydrofuran-2-carboxylic acid methyl ester

Base Information

Chemical Name:(2R,3R,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(phenylselenenyl)tetrahydrofuran-2-carboxylic acid methyl ester
CAS No.:339178-34-6
Molecular Formula:C₁₇H₁₈N₂O₆Se
Molecular Weight:425.3
Hs Code.:

Synonyms:(2R,3R,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(phenylselenenyl)tetrahydrofuran-2-carboxylic acid methyl ester

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Chemical Property of (2R,3R,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(phenylselenenyl)tetrahydrofuran-2-carboxylic acid methyl ester

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Technology Process of (2R,3R,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(phenylselenenyl)tetrahydrofuran-2-carboxylic acid methyl ester

There total 10 articles about (2R,3R,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(phenylselenenyl)tetrahydrofuran-2-carboxylic acid methyl 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: 56.0%

: 5707-04-0
Phenylselenyl chloride

: 339178-25-5
(2S,3R,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)tetrahydrofuran-2-carboxylic acid methyl ester

: (2S,3R,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(phenylselenenyl)tetrahydrofuran-2-carboxylic acid methyl ester

: 339178-34-6
(2R,3R,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(phenylselenenyl)tetrahydrofuran-2-carboxylic acid methyl ester

Guidance literature:: (2S,3R,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)tetrahydrofuran-2-carboxylic acid methyl ester; With lithium diisopropyl amide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; cyclohexane; at -78 - 20 ℃;

With tert.-butyl lithium; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; pentane; at -78 ℃; for 1h;

Phenylselenyl chloride; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; at -78 ℃; for 1h; Further stages.;
DOI:10.1021/jo001223a

Reference yield:

: 124680-51-9
(2R,4R,5R)-1-[5-[bis(4-methoxyphenyl)phenylmethoxymethyl]-4-hydroxytetrahydrofuran-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

: 339178-34-6
(2R,3R,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(phenylselenenyl)tetrahydrofuran-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: 94 percent / imidazole / dimethylformamide / 1.5 h / Heating

2.1: 100 percent / Amberlyst 15-H / methanol / 37 h / 20 °C

3.1: 100 percent / 2,2,6,6-tetramethyl-1-piperidinyl-oxy; iodobenzene diacetate / CH₂Cl₂ / 2 h / 20 °C

4.1: 92 percent / benzene; methanol; hexane / 10 h / 20 °C

5.1: 100 percent / TBAF / tetrahydrofuran / 1.5 h / 0 °C

6.1: LDA / tetrahydrofuran; hexamethylphosphoric acid triamide; cyclohexane / -78 - 20 °C

6.2: t-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide; pentane / 1 h / -78 °C

6.3: 56 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h / -78 °C

With 1H-imidazole; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; Amberlyst 15-H; tetrabutyl ammonium fluoride; lithium diisopropyl amide; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane; cyclohexane; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jo001223a

Reference yield:

: 42926-80-7
5'-O-(4-monomethoxytrityl)-2'-deoxythymidine

: 339178-34-6
(2R,3R,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(phenylselenenyl)tetrahydrofuran-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 9 steps

1.1: 94 percent / Py / 18 h / 0 °C

2.1: 91 percent / NaOH / ethanol; H₂O / 2 h / Heating

3.1: 100 percent / NaOH / ethanol; H₂O / 3 h / Heating

4.1: 94 percent / imidazole / dimethylformamide / 1.5 h / Heating

5.1: 100 percent / Amberlyst 15-H / methanol / 37 h / 20 °C

6.1: 100 percent / 2,2,6,6-tetramethyl-1-piperidinyl-oxy; iodobenzene diacetate / CH₂Cl₂ / 2 h / 20 °C

7.1: 92 percent / benzene; methanol; hexane / 10 h / 20 °C

8.1: 100 percent / TBAF / tetrahydrofuran / 1.5 h / 0 °C

9.1: LDA / tetrahydrofuran; hexamethylphosphoric acid triamide; cyclohexane / -78 - 20 °C

9.2: t-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide; pentane / 1 h / -78 °C

9.3: 56 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h / -78 °C

With pyridine; 1H-imidazole; sodium hydroxide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; Amberlyst 15-H; tetrabutyl ammonium fluoride; lithium diisopropyl amide; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; hexane; dichloromethane; cyclohexane; water; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jo001223a