N⁴-benzoyl-N¹-(2,5-di-O-benzoyl-3-deoxy-3,3-difluoro-α-D-arabinofuranosyl)cytosine

Base Information

• Chemical Name: N⁴-benzoyl-N¹-(2,5-di-O-benzoyl-3-deoxy-3,3-difluoro-α-D-arabinofuranosyl)cytosine
• CAS No.: 885621-70-5
• Molecular Formula: C₃₀H₂₃F₂N₃O₇
• Molecular Weight: 575.525

Synonyms:N⁴-benzoyl-N¹-(2,5-di-O-benzoyl-3-deoxy-3,3-difluoro-α-D-arabinofuranosyl)cytosine

Chemical Property of N⁴-benzoyl-N¹-(2,5-di-O-benzoyl-3-deoxy-3,3-difluoro-α-D-arabinofuranosyl)cytosine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of N⁴-benzoyl-N¹-(2,5-di-O-benzoyl-3-deoxy-3,3-difluoro-α-D-arabinofuranosyl)cytosine

There total 4 articles about N⁴-benzoyl-N¹-(2,5-di-O-benzoyl-3-deoxy-3,3-difluoro-α-D-arabinofuranosyl)cytosine 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: 67.0%

1-O-acetyl-2,5-di-O-benzoyl-3-deoxy-3,3-difluoro-D-arabinofuranose (885621-69-2) + 4-N-benzoylcytosine (26661-13-2) → N4-benzoyl-N1-(2,5-di-O-benzoyl-3-deoxy-3,3-difluoro-α-D-arabinofuranosyl)cytosine (885621-70-5)

Guidance literature:

1-O-acetyl-2,5-di-O-benzoyl-3-deoxy-3,3-difluoro-D-arabinofuranose; 4-N-benzoylcytosine; With N,O-bis-(trimethylsilyl)-acetamide; In acetonitrile; for 0.5h; Heating;

With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at 80 ℃; for 6h;

DOI:10.1021/jo052652h

Reference yield:

((2R,4R,5R)-5-acetoxy-3,3-difluoro-4-hydroxytetrahydrofuran-2-yl)methyl benzoate (885621-68-1) → N4-benzoyl-N1-(2,5-di-O-benzoyl-3-deoxy-3,3-difluoro-α-D-arabinofuranosyl)cytosine (885621-70-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 68 percent / Ph₃P; diethyl azodicarboxylate / toluene / 48 h / Heating

2.1: N,O-bis(trimethylsilyl)acetamide / acetonitrile / 0.5 h / Heating

2.2: 67 percent / TMSOTf / acetonitrile / 6 h / 80 °C

With N,O-bis-(trimethylsilyl)-acetamide; triphenylphosphine; diethylazodicarboxylate; In toluene; acetonitrile; 1.1: Mitsunobu reaction;

DOI:10.1021/jo052652h

Reference yield:

benzoic acid (65-85-0,8013-63-6) → N4-benzoyl-N1-(2,5-di-O-benzoyl-3-deoxy-3,3-difluoro-α-D-arabinofuranosyl)cytosine (885621-70-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 68 percent / Ph₃P; diethyl azodicarboxylate / toluene / 48 h / Heating

2.1: N,O-bis(trimethylsilyl)acetamide / acetonitrile / 0.5 h / Heating

2.2: 67 percent / TMSOTf / acetonitrile / 6 h / 80 °C

With N,O-bis-(trimethylsilyl)-acetamide; triphenylphosphine; diethylazodicarboxylate; In toluene; acetonitrile; 1.1: Mitsunobu reaction;

DOI:10.1021/jo052652h

upstream raw materials:

1-O-acetyl-2,5-di-O-benzoyl-3-deoxy-3,3-difluoro-D-arabinofuranose

4-N-benzoylcytosine

((2R,4R,5R)-5-acetoxy-3,3-difluoro-4-hydroxytetrahydrofuran-2-yl)methyl benzoate

benzoic acid

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