Imidazole-1-carbothioic acid O-[(2R,3R,4R,5R)-5-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-3-yl] ester

Base Information

• Chemical Name: Imidazole-1-carbothioic acid O-[(2R,3R,4R,5R)-5-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-3-yl] ester
• CAS No.: 86314-30-9
• Molecular Formula: C₄₇H₅₁N₅O₈SSi
• Molecular Weight: 874.102

Synonyms:

Chemical Property of Imidazole-1-carbothioic acid O-[(2R,3R,4R,5R)-5-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-3-yl] ester

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

Useful:

Technology Process of Imidazole-1-carbothioic acid O-[(2R,3R,4R,5R)-5-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-3-yl] ester

There total 1 articles about Imidazole-1-carbothioic acid O-[(2R,3R,4R,5R)-5-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-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: 52.0%

5’-O-(1,1-bis(4-methoxyphenyl)-1-phenylmethyl)-2’-O-tert-butyldimethylsilylcytidine (129666-74-6,81256-87-3) + 1,1'-Thiocarbonyldiimidazole (6160-65-2) → Imidazole-1-carbothioic acid O-[(2R,3R,4R,5R)-5-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-3-yl] ester (86314-30-9)

Guidance literature:

In N,N-dimethyl-formamide; for 4h; Ambient temperature;

DOI:10.1016/S0040-4039(00)81550-6

Reference yield: 40.0%

Imidazole-1-carbothioic acid O-[(2R,3R,4R,5R)-5-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-3-yl] ester (86314-30-9) → N-{1-[(2R,3R,5S)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-benzamide (86234-38-0)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; for 4h; Heating;

DOI:10.1016/S0040-4039(00)81550-6

Reference yield:

Imidazole-1-carbothioic acid O-[(2R,3R,4R,5R)-5-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-3-yl] ester (86314-30-9) → N4-benzoyl-5'-O-dimethoxytrityl-3'-deoxyribicytidine (86234-45-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 40 percent / 2,2'-azobis(2-methylpropionitrile), (n-Bu)3SnH / toluene / 4 h / Heating

2: 90 percent / TBAF / ethanol

With 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; In ethanol; toluene;

DOI:10.1016/S0040-4039(00)81550-6

upstream raw materials:

5’-O-(1,1-bis(4-methoxyphenyl)-1-phenylmethyl)-2’-O-tert-butyldimethylsilylcytidine

1,1'-Thiocarbonyldiimidazole

Downstream raw materials:

N-{1-[(2R,3R,5S)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-benzamide

N⁴-benzoyl-5'-O-dimethoxytrityl-3'-deoxyribicytidine

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