N⁶-benzoyl-9-(2'-O-acetyl-5'-O-benzoyl-3'-C-cyano-3'-deoxy-β-L-ribofuranosyl)adenine

Base Information

• Chemical Name: N⁶-benzoyl-9-(2'-O-acetyl-5'-O-benzoyl-3'-C-cyano-3'-deoxy-β-L-ribofuranosyl)adenine
• CAS No.: 612485-22-0
• Molecular Formula: C₂₇H₂₂N₆O₆
• Molecular Weight: 526.508

Synonyms:N⁶-benzoyl-9-(2'-O-acetyl-5'-O-benzoyl-3'-C-cyano-3'-deoxy-β-L-ribofuranosyl)adenine

Chemical Property of N⁶-benzoyl-9-(2'-O-acetyl-5'-O-benzoyl-3'-C-cyano-3'-deoxy-β-L-ribofuranosyl)adenine

Chemical Property:

Purity/Quality:

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Technology Process of N⁶-benzoyl-9-(2'-O-acetyl-5'-O-benzoyl-3'-C-cyano-3'-deoxy-β-L-ribofuranosyl)adenine

There total 5 articles about N⁶-benzoyl-9-(2'-O-acetyl-5'-O-benzoyl-3'-C-cyano-3'-deoxy-β-L-ribofuranosyl)adenine 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: 75.0%

N-benzoyladenine (4005-49-6) + 1,2-di-O-acetyl-5-O-benzoyl-3-C-cyano-3-deoxy-L-ribofuranose (612485-18-4) → N6-benzoyl-9-(2'-O-acetyl-5'-O-benzoyl-3'-C-cyano-3'-deoxy-β-L-ribofuranosyl)adenine (612485-22-0)

Guidance literature:

With N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; In acetonitrile; for 24h; Heating;

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

Reference yield:

benzoyl chloride (98-88-4) → N6-benzoyl-9-(2'-O-acetyl-5'-O-benzoyl-3'-C-cyano-3'-deoxy-β-L-ribofuranosyl)adenine (612485-22-0)

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: 75 percent / N,O-bis(trimethylsilyl)acetamide; TMSOTf / acetonitrile / 24 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 → N6-benzoyl-9-(2'-O-acetyl-5'-O-benzoyl-3'-C-cyano-3'-deoxy-β-L-ribofuranosyl)adenine (612485-22-0)

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: 75 percent / N,O-bis(trimethylsilyl)acetamide; TMSOTf / acetonitrile / 24 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:

N-benzoyladenine

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:

9-(5'-O-benzoyl-3'-C-cyano-2',3'-didehydro-2',3'-dideoxy-β-L-ribofuranosyl)adenosine

N⁶-benzoyl-9-(5'-O-benzoyl-3'-C-cyano-2',3'-didehydro-2',3'-dideoxy-β-L-ribofuranosyl)adenosine

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