5'-O-benzoyl-3'-O-tetrahydrofuranyl-2'-O-imidazolylthiocarbonyl-O⁴-methyl-6,3'-methanouridine

Base Information

• Chemical Name: 5'-O-benzoyl-3'-O-tetrahydrofuranyl-2'-O-imidazolylthiocarbonyl-O⁴-methyl-6,3'-methanouridine
• CAS No.: 115848-04-9
• Molecular Formula: C₂₆H₂₆N₄O₈S
• Molecular Weight: 554.58

Synonyms:5'-O-benzoyl-3'-O-tetrahydrofuranyl-2'-O-imidazolylthiocarbonyl-O⁴-methyl-6,3'-methanouridine

Chemical Property of 5'-O-benzoyl-3'-O-tetrahydrofuranyl-2'-O-imidazolylthiocarbonyl-O⁴-methyl-6,3'-methanouridine

Chemical Property:

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Technology Process of 5'-O-benzoyl-3'-O-tetrahydrofuranyl-2'-O-imidazolylthiocarbonyl-O⁴-methyl-6,3'-methanouridine

There total 13 articles about 5'-O-benzoyl-3'-O-tetrahydrofuranyl-2'-O-imidazolylthiocarbonyl-O⁴-methyl-6,3'-methanouridine 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: 72.0%

5'-O-benzoyl-3'-O-tetrahydrofuranyl-O4-methyl-6,3'-methanouridine (115848-03-8) + 1,1'-Thiocarbonyldiimidazole (6160-65-2) → 5'-O-benzoyl-3'-O-tetrahydrofuranyl-2'-O-imidazolylthiocarbonyl-O4-methyl-6,3'-methanouridine (115848-04-9)

Guidance literature:

In N,N-dimethyl-formamide; Ambient temperature;

DOI:10.1248/cpb.36.162

Reference yield:

2,4-dimethoxy-6-methylpyrimidine (7781-23-9) → 5'-O-benzoyl-3'-O-tetrahydrofuranyl-2'-O-imidazolylthiocarbonyl-O4-methyl-6,3'-methanouridine (115848-04-9)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) n-BuLi / 1.) THF/n-hexane, -35 deg C, 1 h, 2.) THF, -35 deg C, 1 h

2: tetrabutylammonium fluoride / tetrahydrofuran / 0.17 h / Ambient temperature

3: pyridine / Ambient temperature

4: 90 percent trifluoroacetic acid / 1.5 h / Ambient temperature

5: Et₃N / CH₂Cl₂ / 2 h

6: 82 percent / stannic chloride / acetonitrile / 3 h / Ambient temperature

7: 82 percent / p-toluenesulfonic acid / dioxane / Ambient temperature

8: 80 percent / MeOH, Et₃N / 3 h / Ambient temperature

9: 72 percent / dimethylformamide / Ambient temperature

With pyridine; methanol; n-butyllithium; tetrabutyl ammonium fluoride; tin(IV) chloride; toluene-4-sulfonic acid; triethylamine; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1248/cpb.36.162

Reference yield:

benzoyl chloride (98-88-4) → 5'-O-benzoyl-3'-O-tetrahydrofuranyl-2'-O-imidazolylthiocarbonyl-O4-methyl-6,3'-methanouridine (115848-04-9)

Guidance literature:

Multi-step reaction with 7 steps

1: pyridine / Ambient temperature

2: 90 percent trifluoroacetic acid / 1.5 h / Ambient temperature

3: Et₃N / CH₂Cl₂ / 2 h

4: 82 percent / stannic chloride / acetonitrile / 3 h / Ambient temperature

5: 82 percent / p-toluenesulfonic acid / dioxane / Ambient temperature

6: 80 percent / MeOH, Et₃N / 3 h / Ambient temperature

7: 72 percent / dimethylformamide / Ambient temperature

With pyridine; methanol; tin(IV) chloride; toluene-4-sulfonic acid; triethylamine; trifluoroacetic acid; In 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1248/cpb.36.162

upstream raw materials:

5'-O-benzoyl-3'-O-tetrahydrofuranyl-O⁴-methyl-6,3'-methanouridine

1,1'-Thiocarbonyldiimidazole

2,4-dimethoxy-6-methylpyrimidine

benzoyl chloride

Downstream raw materials:

5'-O-benzoyl-2'-deoxy-O⁴-methyl-6,3'-methanouridine

Benzoic acid (1R,9S,10R)-5-methoxy-3-oxo-9-(tetrahydro-furan-2-yloxy)-11-oxa-2,4-diaza-tricyclo[7.2.1.0^2,7]dodeca-4,6-dien-10-ylmethyl ester

5'-O-benzoyl-3'-O-tetrahydrofuranyl-O⁴-methyl-6,3'-methanouridine

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