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

Base Information

• Chemical Name: N⁴-benzoyl-N¹-(2-O-benzyl-5-O-benzoyl-3-deoxy-3,3-difluoro-α-D-arabinofuranosyl)cytosine
• CAS No.: 634181-85-4
• Molecular Formula: C₃₀H₂₅F₂N₃O₆
• Molecular Weight: 561.542

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

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

Chemical Property:

Purity/Quality:

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Technology Process of N⁴-benzoyl-N¹-(2-O-benzyl-5-O-benzoyl-3-deoxy-3,3-difluoro-α-D-arabinofuranosyl)cytosine

There total 12 articles about N⁴-benzoyl-N¹-(2-O-benzyl-5-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: 35.0%

4-N-benzoylcytosine (26661-13-2) + 1-O-acetyl-2-O-benzyl-5-O-benzoyl-3-deoxy-3,3-difluoro-α-D-arabinofuranose (634181-84-3) → N4-benzoyl-N1-(2-O-benzyl-5-O-benzoyl-3-deoxy-3,3-difluoro-β-D-arabinofuranosyl)cytosine (634181-86-5) + N4-benzoyl-N1-(2-O-benzyl-5-O-benzoyl-3-deoxy-3,3-difluoro-α-D-arabinofuranosyl)cytosine (634181-85-4)

Guidance literature:

With N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at 0 - 80 ℃; for 36h;

DOI:10.1021/jo034512i

Reference yield:

benzoyl chloride (98-88-4) → N4-benzoyl-N1-(2-O-benzyl-5-O-benzoyl-3-deoxy-3,3-difluoro-α-D-arabinofuranosyl)cytosine (634181-85-4)

Guidance literature:

Multi-step reaction with 5 steps

1: pyridine / CH₂Cl₂ / 2 h / -70 °C

2: aq. AcOH / 1.5 h / 50 °C

3: aq. NaIO₄ / 1.5 h / 20 °C

4: 94 percent / DMAP / CH₂Cl₂ / 20 °C

5: 35 percent / N,O-bis(trimethylsilyl)acetamide; TMSOTf / acetonitrile / 36 h / 0 - 80 °C

With pyridine; dmap; sodium periodate; N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; acetic acid; In dichloromethane; acetonitrile;

DOI:10.1021/jo034512i

Reference yield:

benzyl bromide (100-39-0) → N4-benzoyl-N1-(2-O-benzyl-5-O-benzoyl-3-deoxy-3,3-difluoro-α-D-arabinofuranosyl)cytosine (634181-85-4)

Guidance literature:

Multi-step reaction with 7 steps

1: NaH; Bu₄NI / tetrahydrofuran / 0 - 20 °C

2: 47.5 percent / OsO₄; NMNO; H₂O / acetone / 48 h / 20 °C

3: 90 percent / pyridine / CH₂Cl₂ / 2 h / -70 °C

4: aq. AcOH / 1.5 h / 50 °C

5: 4.328 g / aq. NaIO₄ / 1.5 h / 20 °C

6: 94 percent / DMAP / CH₂Cl₂ / 20 °C

7: 35 percent / N,O-bis(trimethylsilyl)acetamide; TMSOTf / acetonitrile / 36 h / 0 - 80 °C

With pyridine; dmap; sodium periodate; osmium(VIII) oxide; N,O-bis-(trimethylsilyl)-acetamide; bis-(2-chloro-ethyl)-methyl-amine oxide; trimethylsilyl trifluoromethanesulfonate; water; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; In tetrahydrofuran; dichloromethane; acetone; acetonitrile;

DOI:10.1021/jo034512i

upstream raw materials:

4-N-benzoylcytosine

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

benzyl bromide

benzoyl chloride

Downstream raw materials:

N¹-(2-O-benzyl-3-deoxy-3,3-difluoro-α-D-arabinofuranosyl)cytosine

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