(+)-(2S,4S)-N⁴-benzoyl-1-<2-<(benzoyloxy)methyl>-1,3-dioxolan-4-yl>-5-fluorocytosine

Base Information

• Chemical Name: (+)-(2S,4S)-N⁴-benzoyl-1-<2-<(benzoyloxy)methyl>-1,3-dioxolan-4-yl>-5-fluorocytosine
• CAS No.: 146996-29-4
• Molecular Formula: C₂₂H₁₈FN₃O₆
• Molecular Weight: 439.4

Synonyms:(+)-(2S,4S)-N⁴-benzoyl-1-<2-<(benzoyloxy)methyl>-1,3-dioxolan-4-yl>-5-fluorocytosine

Chemical Property of (+)-(2S,4S)-N⁴-benzoyl-1-<2-<(benzoyloxy)methyl>-1,3-dioxolan-4-yl>-5-fluorocytosine

Chemical Property:

Purity/Quality:

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Technology Process of (+)-(2S,4S)-N⁴-benzoyl-1-<2-<(benzoyloxy)methyl>-1,3-dioxolan-4-yl>-5-fluorocytosine

There total 7 articles about (+)-(2S,4S)-N⁴-benzoyl-1-<2-<(benzoyloxy)methyl>-1,3-dioxolan-4-yl>-5-fluorocytosine 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: 49.0%

(2S,4RS)-4-acetoxy-2-<(benzoyloxy)methyl>dioxolane (214273-21-9,145354-82-1) + C17H24FN3O2Si2 → (+)-(2S,4S)-N4-benzoyl-1-<2-<(benzoyloxy)methyl>-1,3-dioxolan-4-yl>-5-fluorocytosine (146996-29-4) + (+)-(2S,4R)-N4-benzoyl-1-<2-<(benzoyloxy)methyl>-1,3-dioxolan-4-yl>-5-fluorocytosine (146996-30-7)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; for 1.5h; Ambient temperature;

DOI:10.1021/jm00057a001

Reference yield: 18.0%

(2S,4RS)-4-acetoxy-2-<(benzoyloxy)methyl>dioxolane (214273-21-9,145354-82-1) + N-benzoyl-5-fluorocytosine (10357-07-0) → (+)-(2S,4S)-N4-benzoyl-1-<2-<(benzoyloxy)methyl>-1,3-dioxolan-4-yl>-5-fluorocytosine (146996-29-4) + (+)-(2S,4R)-N4-benzoyl-1-<2-<(benzoyloxy)methyl>-1,3-dioxolan-4-yl>-5-fluorocytosine (146996-30-7)

Guidance literature:

N-benzoyl-5-fluorocytosine; With ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane; for 14h; Reflux;

(2S,4RS)-4-acetoxy-2-<(benzoyloxy)methyl>dioxolane; With trimethylsilyl trifluoromethanesulfonate; In 1,2-dichloro-ethane; at 20 ℃; for 2h;

Reference yield:

benzoyl chloride (98-88-4) → (+)-(2S,4S)-N4-benzoyl-1-<2-<(benzoyloxy)methyl>-1,3-dioxolan-4-yl>-5-fluorocytosine (146996-29-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 83.4 percent / pyridine / CH₂Cl₂ / 2 h

2: 99.2 percent / p-TsOH / methanol / 3 h / Ambient temperature

3: NaIO₄, RuO₂ / H₂O; CCl₄; acetonitrile / 5 h

4: pyridine / tetrahydrofuran / 0.75 h

5: 49 percent / TMSOTf / CH₂Cl₂ / 1.5 h / Ambient temperature

With pyridine; ruthenium(IV) oxide; sodium periodate; trimethylsilyl trifluoromethanesulfonate; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; water; acetonitrile;

DOI:10.1021/jm00057a001

upstream raw materials:

(2S,4RS)-4-acetoxy-2-<(benzoyloxy)methyl>dioxolane

benzoyl chloride

(2S,4S)-2-Benzoyloxymethyl-[1,3]dioxolane-4-carboxylic acid

(+)-(1'S,2S,4S)-4-(1,2-dihydroxyethyl)-2-<(benzoyloxy)methyl>dioxolane

Downstream raw materials:

4-amino-5-fluoro-1-((2S,4S)-2-(hydroxymethyl)-1,3-dioxolan-4-yl)pyrimidin-2(1H)-one

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