1-(2'-O-acetyl-5'-O-benzoyl-3'-C-cyano-3'-deoxy-β-L-ribofuranosyl)-N⁴-benzoylcytosine

Base Information

• Chemical Name: 1-(2'-O-acetyl-5'-O-benzoyl-3'-C-cyano-3'-deoxy-β-L-ribofuranosyl)-N⁴-benzoylcytosine
• CAS No.: 612485-21-9
• Molecular Formula: C₂₆H₂₂N₄O₇
• Molecular Weight: 502.483

Synonyms:1-(2'-O-acetyl-5'-O-benzoyl-3'-C-cyano-3'-deoxy-β-L-ribofuranosyl)-N⁴-benzoylcytosine

Chemical Property of 1-(2'-O-acetyl-5'-O-benzoyl-3'-C-cyano-3'-deoxy-β-L-ribofuranosyl)-N⁴-benzoylcytosine

Chemical Property:

Purity/Quality:

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Technology Process of 1-(2'-O-acetyl-5'-O-benzoyl-3'-C-cyano-3'-deoxy-β-L-ribofuranosyl)-N⁴-benzoylcytosine

There total 5 articles about 1-(2'-O-acetyl-5'-O-benzoyl-3'-C-cyano-3'-deoxy-β-L-ribofuranosyl)-N⁴-benzoylcytosine 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: 80.0%

4-N-benzoylcytosine (26661-13-2) + 1,2-di-O-acetyl-5-O-benzoyl-3-C-cyano-3-deoxy-L-ribofuranose (612485-18-4) → 1-(2'-O-acetyl-5'-O-benzoyl-3'-C-cyano-3'-deoxy-β-L-ribofuranosyl)-N4-benzoylcytosine (612485-21-9)

Guidance literature:

With N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; In acetonitrile; for 10h; Heating;

DOI:10.1016/S0040-4020(03)01074-3

Reference yield:

benzoyl chloride (98-88-4) → 1-(2'-O-acetyl-5'-O-benzoyl-3'-C-cyano-3'-deoxy-β-L-ribofuranosyl)-N4-benzoylcytosine (612485-21-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / pyridine / CH₂Cl₂ / 1 h / 20 °C

2: CF₃CO₂H / H₂O / 6 h

3: 32 g / pyridine / 12 h / 20 °C

4: 80 percent / N,O-bis(trimethylsilyl)acetamide; TMSOTf / acetonitrile / 10 h / Heating

With pyridine; N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; trifluoroacetic acid; In dichloromethane; water; acetonitrile;

DOI:10.1016/S0040-4020(03)01074-3

Reference yield:

3-C-cyano-3-deoxy-1,2-O-isopropylidene-α-L-ribofuranose → 1-(2'-O-acetyl-5'-O-benzoyl-3'-C-cyano-3'-deoxy-β-L-ribofuranosyl)-N4-benzoylcytosine (612485-21-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / pyridine / CH₂Cl₂ / 1 h / 20 °C

2: CF₃CO₂H / H₂O / 6 h

3: 32 g / pyridine / 12 h / 20 °C

4: 80 percent / N,O-bis(trimethylsilyl)acetamide; TMSOTf / acetonitrile / 10 h / Heating

With pyridine; N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; trifluoroacetic acid; In dichloromethane; water; acetonitrile;

DOI:10.1016/S0040-4020(03)01074-3

upstream raw materials:

4-N-benzoylcytosine

1,2-di-O-acetyl-5-O-benzoyl-3-C-cyano-3-deoxy-L-ribofuranose

benzoyl chloride

Benzoic acid (2R,3R,4S)-3-cyano-4,5-dihydroxy-tetrahydro-furan-2-ylmethyl ester

Downstream raw materials:

1-(5'-O-benzoyl-3'-C-cyano-2,'3'-didehydro-2',3'-dideoxy-β-L-ribofuranosyl)cytidine

1-(5'-O-benzoyl-3'-C-cyano-2,'3'-didehydro-2',3'-dideoxy-β-L-ribofuranosyl)-N⁴-benzoylcytidine

1-(5'-O-benzoyl-3'-C-cyano-3'-deoxy-β-L-ribofuranosyl)cytosine

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