Imidazole-1-carbothioic acid O-[(2R,3R,4R,5R)-4-acetylsulfanylmethyl-5-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl] ester

Base Information

• Chemical Name: Imidazole-1-carbothioic acid O-[(2R,3R,4R,5R)-4-acetylsulfanylmethyl-5-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl] ester
• CAS No.: 208463-30-3
• Molecular Formula: C₃₄H₄₀N₄O₆S₂Si
• Molecular Weight: 692.932

Synonyms:Imidazole-1-carbothioic acid O-[(2R,3R,4R,5R)-4-acetylsulfanylmethyl-5-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl] ester

Chemical Property of Imidazole-1-carbothioic acid O-[(2R,3R,4R,5R)-4-acetylsulfanylmethyl-5-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl] ester

Chemical Property:

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Technology Process of Imidazole-1-carbothioic acid O-[(2R,3R,4R,5R)-4-acetylsulfanylmethyl-5-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl] ester

There total 9 articles about Imidazole-1-carbothioic acid O-[(2R,3R,4R,5R)-4-acetylsulfanylmethyl-5-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl] 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:

Benzoic acid (2R,3S,4R)-4-hydroxy-2-(2-hydroxy-ethyl)-5-methoxy-tetrahydro-furan-3-ylmethyl ester (441044-21-9) → Imidazole-1-carbothioic acid O-[(2R,3R,4R,5R)-4-acetylsulfanylmethyl-5-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl] ester (208463-30-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: imidazole; acetic acid / dimethylformamide / 0.83 h

2.1: NaOH / methanol; H₂O

3.1: 21.90 g / 4-dimethylaminopyridine; triethylamine / tetrahydrofuran; methanol / 1.17 h

4.1: N-methyl-N-trimethylsilyltrifluoroacetamide / acetonitrile

4.2: SnCl₄ / acetonitrile / 20 °C

5.1: NaOH / H₂O; methanol

6.1: tetrahydrofuran / 20 °C

With 1H-imidazole; dmap; sodium hydroxide; N-methyl-N-trimethylsilyl-2,2,2-trifluoroacetamide; acetic acid; triethylamine; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide; acetonitrile; 4.1: Vorbrueggen reaction;

DOI:10.1021/jo0003910

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → Imidazole-1-carbothioic acid O-[(2R,3R,4R,5R)-4-acetylsulfanylmethyl-5-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl] ester (208463-30-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: imidazole; acetic acid / dimethylformamide / 0.83 h

2.1: NaOH / methanol; H₂O

3.1: 21.90 g / 4-dimethylaminopyridine; triethylamine / tetrahydrofuran; methanol / 1.17 h

4.1: N-methyl-N-trimethylsilyltrifluoroacetamide / acetonitrile

4.2: SnCl₄ / acetonitrile / 20 °C

5.1: NaOH / H₂O; methanol

6.1: tetrahydrofuran / 20 °C

With 1H-imidazole; dmap; sodium hydroxide; N-methyl-N-trimethylsilyl-2,2,2-trifluoroacetamide; acetic acid; triethylamine; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide; acetonitrile; 4.1: Vorbrueggen reaction;

DOI:10.1021/jo0003910

Reference yield:

Benzoic acid (2R,3S,4R)-2-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-hydroxy-5-methoxy-tetrahydro-furan-3-ylmethyl ester → Imidazole-1-carbothioic acid O-[(2R,3R,4R,5R)-4-acetylsulfanylmethyl-5-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl] ester (208463-30-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: NaOH / methanol; H₂O

2.1: 21.90 g / 4-dimethylaminopyridine; triethylamine / tetrahydrofuran; methanol / 1.17 h

3.1: N-methyl-N-trimethylsilyltrifluoroacetamide / acetonitrile

3.2: SnCl₄ / acetonitrile / 20 °C

4.1: NaOH / H₂O; methanol

5.1: tetrahydrofuran / 20 °C

With dmap; sodium hydroxide; N-methyl-N-trimethylsilyl-2,2,2-trifluoroacetamide; triethylamine; In tetrahydrofuran; methanol; water; acetonitrile; 3.1: Vorbrueggen reaction;

DOI:10.1021/jo0003910

upstream raw materials:

1,1'-Thiocarbonyldiimidazole

Thioacetic acid S-[(2R,3S,4R,5R)-2-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-ylmethyl] ester

1-{(2R,3R,4S,5R)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-3-hydroxy-4-hydroxymethyl-tetrahydro-furan-2-yl}-5-methyl-1H-pyrimidine-2,4-dione

Benzoic acid (2R,3S,4R)-4-hydroxy-2-(2-hydroxy-ethyl)-5-methoxy-tetrahydro-furan-3-ylmethyl ester

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