N⁴-benzoyl-1-(2,5-di-O-benzoyl-3-deoxy-3,3-difluoro-4-thio-β-L-xylofuranosyl)cytosine

Base Information

• Chemical Name: N⁴-benzoyl-1-(2,5-di-O-benzoyl-3-deoxy-3,3-difluoro-4-thio-β-L-xylofuranosyl)cytosine
• CAS No.: 921202-91-7
• Molecular Formula: C₃₀H₂₃F₂N₃O₆S
• Molecular Weight: 591.592

Synonyms:N⁴-benzoyl-1-(2,5-di-O-benzoyl-3-deoxy-3,3-difluoro-4-thio-β-L-xylofuranosyl)cytosine

Chemical Property of N⁴-benzoyl-1-(2,5-di-O-benzoyl-3-deoxy-3,3-difluoro-4-thio-β-L-xylofuranosyl)cytosine

Chemical Property:

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Technology Process of N⁴-benzoyl-1-(2,5-di-O-benzoyl-3-deoxy-3,3-difluoro-4-thio-β-L-xylofuranosyl)cytosine

There total 10 articles about N⁴-benzoyl-1-(2,5-di-O-benzoyl-3-deoxy-3,3-difluoro-4-thio-β-L-xylofuranosyl)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: 59.0%

1-O-acetyl-2,5-di-O-benzoyl-3-deoxy-3,3-difluoro-4-thio-β-L-xylofuranose (921202-77-9) + 4-N-benzoylcytosine (26661-13-2) → N4-benzoyl-1-(2,5-di-O-benzoyl-3-deoxy-3,3-difluoro-4-thio-β-L-xylofuranosyl)cytosine (921202-91-7)

Guidance literature:

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

With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at 0 - 80 ℃;

DOI:10.1021/ol062576k

Reference yield:

Benzoic acid (2R,4R)-4-benzyloxy-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3,3-difluoro-2-trifluoromethanesulfonyloxy-butyl ester → N4-benzoyl-1-(2,5-di-O-benzoyl-3-deoxy-3,3-difluoro-4-thio-β-L-xylofuranosyl)cytosine (921202-91-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 86 percent / CsF / dimethylformamide / 13 h / 20 °C

2.1: CF₃COOH / tetrahydrofuran; H₂O / 1 h

2.2: NaIO₄ / methanol; H₂O / 1.5 h

2.3: 64 percent / HCl / methanol

3.1: 97 percent / DMAP / CH₂Cl₂ / 0.5 h / 20 °C

4.1: 87 percent / NaBrO₃ / ethyl acetate; H₂O / 0.33 h / 20 °C

5.1: 91 percent / Et₃N; DMAP / CH₂Cl₂ / 0.33 h / 20 °C

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

6.2: 59 percent / TMSOTf / acetonitrile / 0 - 80 °C

With dmap; sodium bromate; N,O-bis-(trimethylsilyl)-acetamide; triethylamine; cesium fluoride; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; 6.1: Vorbrueggen glycosylation;

DOI:10.1021/ol062576k

Reference yield:

1-O-acetyl-5-O-benzoyl-3-deoxy-3,3-difluoro-4-thio-β-L-xylofuranose (921202-72-4) → N4-benzoyl-1-(2,5-di-O-benzoyl-3-deoxy-3,3-difluoro-4-thio-β-L-xylofuranosyl)cytosine (921202-91-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 91 percent / Et₃N; DMAP / CH₂Cl₂ / 0.33 h / 20 °C

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

2.2: 59 percent / TMSOTf / acetonitrile / 0 - 80 °C

With dmap; N,O-bis-(trimethylsilyl)-acetamide; triethylamine; In dichloromethane; acetonitrile; 2.1: Vorbrueggen glycosylation;

DOI:10.1021/ol062576k

upstream raw materials:

1-O-acetyl-2,5-di-O-benzoyl-3-deoxy-3,3-difluoro-4-thio-β-L-xylofuranose

4-N-benzoylcytosine

1-O-acetyl-5-O-benzoyl-3-deoxy-3,3-difluoro-4-thio-β-L-xylofuranose

1-O-acetyl-2-O-benzyl-5-O-benzoyl-3-deoxy-3,3-difluoro-4-thio-L-xylofuranose

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