3-Benzoyl-1-((3S,5R)-5-hydroxymethyl-4-methylene-tetrahydro-thiophen-3-yl)-5-methyl-1H-pyrimidine-2,4-dione

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Chemical Name:3-Benzoyl-1-((3S,5R)-5-hydroxymethyl-4-methylene-tetrahydro-thiophen-3-yl)-5-methyl-1H-pyrimidine-2,4-dione
CAS No.:688797-66-2
Molecular Formula:C₁₈H₁₈N₂O₄S
Molecular Weight:358.418
Hs Code.:

Synonyms:3-Benzoyl-1-((3S,5R)-5-hydroxymethyl-4-methylene-tetrahydro-thiophen-3-yl)-5-methyl-1H-pyrimidine-2,4-dione

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Chemical Property of 3-Benzoyl-1-((3S,5R)-5-hydroxymethyl-4-methylene-tetrahydro-thiophen-3-yl)-5-methyl-1H-pyrimidine-2,4-dione

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Technology Process of 3-Benzoyl-1-((3S,5R)-5-hydroxymethyl-4-methylene-tetrahydro-thiophen-3-yl)-5-methyl-1H-pyrimidine-2,4-dione

There total 7 articles about 3-Benzoyl-1-((3S,5R)-5-hydroxymethyl-4-methylene-tetrahydro-thiophen-3-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: 42.0%

: 4330-20-5
N-3-benzoylthymine

: 688797-29-7
(3R,5R)-5-[(tert-butyldiphenylsilyloxy)methyl]-4-methylenetetrahydrothiophen-3-ol

: 688797-66-2
3-Benzoyl-1-((3S,5R)-5-hydroxymethyl-4-methylene-tetrahydro-thiophen-3-yl)-5-methyl-1H-pyrimidine-2,4-dione

Guidance literature:: N-3-benzoylthymine; (3R,5R)-5-[(tert-butyldiphenylsilyloxy)methyl]-4-methylenetetrahydrothiophen-3-ol; With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 0 ℃; for 1h;

With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 20 ℃; for 12h;
DOI:10.1021/jo035735b

Reference yield:

: 688797-27-5
(3R,5R)-5-(hydroxymethyl)-4-methylenetetrahydrothiophen-3-ol

: 688797-66-2
3-Benzoyl-1-((3S,5R)-5-hydroxymethyl-4-methylene-tetrahydro-thiophen-3-yl)-5-methyl-1H-pyrimidine-2,4-dione

Guidance literature:: Multi-step reaction with 2 steps

1.1: 91 percent / imidazole / dimethylformamide / 24 h / 20 °C

2.1: triphenylphosphine; diethyl azodicarboxylate / tetrahydrofuran / 1 h / 0 °C

2.2: 42 percent / acetic acid; tetrabutylammonium fluoride / tetrahydrofuran / 12 h / 20 °C

With 1H-imidazole; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; N,N-dimethyl-formamide; 2.1: Mitsunobu condensation;
DOI:10.1021/jo035735b

Reference yield:

: methyl 2,5-di-O-benzyl-3-deoxy-3-methylene-D-erythro-pentofuranoside

: 688797-66-2
3-Benzoyl-1-((3S,5R)-5-hydroxymethyl-4-methylene-tetrahydro-thiophen-3-yl)-5-methyl-1H-pyrimidine-2,4-dione

Guidance literature:: Multi-step reaction with 7 steps

1.1: 74 percent / aqueous HCl / dioxane / 24 h / 20 °C

2.1: 91 percent / lithium borohydride / tetrahydrofuran / 24 h / 20 °C

3.1: 70 percent / pyridine / CH₂Cl₂ / 3 h / 20 °C

4.1: 50 percent / sodium sulfide / dimethylformamide / 4 h / 0 °C

5.1: 85 percent / boron trichloride / CH₂Cl₂ / 3 h / -78 °C

6.1: 91 percent / imidazole / dimethylformamide / 24 h / 20 °C

7.1: triphenylphosphine; diethyl azodicarboxylate / tetrahydrofuran / 1 h / 0 °C

7.2: 42 percent / acetic acid; tetrabutylammonium fluoride / tetrahydrofuran / 12 h / 20 °C

With pyridine; 1H-imidazole; hydrogenchloride; sodium sulfide; lithium borohydride; boron trichloride; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide; 7.1: Mitsunobu condensation;
DOI:10.1021/jo035735b