1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-5-phenylselenenyltetrahydrofuran-2-yl)-5-methyl-1H-pyrimidine-2,4-dione

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Chemical Name:1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-5-phenylselenenyltetrahydrofuran-2-yl)-5-methyl-1H-pyrimidine-2,4-dione
CAS No.:164864-68-0
Molecular Formula:C₁₆H₁₈N₂O₅Se
Molecular Weight:397.289
Hs Code.:

Synonyms:1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-5-phenylselenenyltetrahydrofuran-2-yl)-5-methyl-1H-pyrimidine-2,4-dione

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Chemical Property of 1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-5-phenylselenenyltetrahydrofuran-2-yl)-5-methyl-1H-pyrimidine-2,4-dione

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Technology Process of 1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-5-phenylselenenyltetrahydrofuran-2-yl)-5-methyl-1H-pyrimidine-2,4-dione

There total 14 articles about 1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-5-phenylselenenyltetrahydrofuran-2-yl)-5-methyl-1H-pyrimidine-2,4-dione 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: 82.0%

: 1-[(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-hydroxymethyl-5-phenylselanyl-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

: 164864-68-0
1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-5-phenylselenenyltetrahydrofuran-2-yl)-5-methyl-1H-pyrimidine-2,4-dione

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃;
DOI:10.1016/S0040-4039(00)77005-5

Reference yield: 68.0%

: 339178-17-5
(2S,4S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(phenylselenenyl)tetrahydrofuran-2-carboxylic acid tert-butyl ester

: 164864-68-0
1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-5-phenylselenenyltetrahydrofuran-2-yl)-5-methyl-1H-pyrimidine-2,4-dione

Guidance literature:: With lithium borohydride; In tetrahydrofuran; at 20 ℃; for 1h;
DOI:10.1021/jo001223a

Reference yield:

: 127244-82-0
(2S,3S,5R)-3-(tert-butyldiphenylsilanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydrofuran-2-carboxylic acid

: 164864-68-0
1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-5-phenylselenenyltetrahydrofuran-2-yl)-5-methyl-1H-pyrimidine-2,4-dione

Guidance literature:: Multi-step reaction with 4 steps

1.1: 100 percent / DMAP; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 23.5 h / 0 - 20 °C

2.1: 97 percent / TBAF / tetrahydrofuran / 1.5 h / 0 °C

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

3.2: tBuLi / tetrahydrofuran; hexamethylphosphoric acid triamide; pentane / 1 h / -78 °C

3.3: 57 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h / -78 °C

4.1: 68 percent / LiBH₄ / tetrahydrofuran / 1 h / 20 °C

With dmap; lithium borohydride; tetrabutyl ammonium fluoride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; lithium diisopropyl amide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; cyclohexane;
DOI:10.1021/jo001223a