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

Base Information

• Chemical Name: N⁶-benzoyl-9-(5'-O-benzoyl-3'-C-cyano-2',3'-didehydro-2',3'-dideoxy-β-L-ribofuranosyl)adenosine
• CAS No.: 612485-32-2
• Molecular Formula: C₂₅H₁₈N₆O₄
• Molecular Weight: 466.456

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

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

Chemical Property:

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

There total 5 articles about N⁶-benzoyl-9-(5'-O-benzoyl-3'-C-cyano-2',3'-didehydro-2',3'-dideoxy-β-L-ribofuranosyl)adenosine 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: 94.0%

N6-benzoyl-9-(2'-O-acetyl-5'-O-benzoyl-3'-C-cyano-3'-deoxy-β-L-ribofuranosyl)adenine (612485-22-0) → N6-benzoyl-9-(5'-O-benzoyl-3'-C-cyano-2',3'-didehydro-2',3'-dideoxy-β-L-ribofuranosyl)adenosine (612485-32-2)

Guidance literature:

With dmap; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃; for 1h;

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

Reference yield:

benzoyl chloride (98-88-4) → N6-benzoyl-9-(5'-O-benzoyl-3'-C-cyano-2',3'-didehydro-2',3'-dideoxy-β-L-ribofuranosyl)adenosine (612485-32-2)

Guidance literature:

Multi-step reaction with 5 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

5: 94 percent / 4-(dimethylamino)pyridine; 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 1 h / 20 °C

With pyridine; dmap; N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; 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-(5'-O-benzoyl-3'-C-cyano-2',3'-didehydro-2',3'-dideoxy-β-L-ribofuranosyl)adenosine (612485-32-2)

Guidance literature:

Multi-step reaction with 5 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

5: 94 percent / 4-(dimethylamino)pyridine; 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 1 h / 20 °C

With pyridine; dmap; N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; In dichloromethane; water; acetonitrile;

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

upstream raw materials:

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

benzoyl chloride

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

5-O-benzoyl-3-C-cyano-3-deoxy-1,2-O-isopropylidene-α-L-ribofuranose

Downstream raw materials:

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

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