1-(3-deoxy-3-fluoro-4,6-O-isopropylidene-β-D-glucopyranosyl-2-ulose)-N⁴-benzoylcytosine

Base Information

• Chemical Name: 1-(3-deoxy-3-fluoro-4,6-O-isopropylidene-β-D-glucopyranosyl-2-ulose)-N⁴-benzoylcytosine
• CAS No.: 924279-88-9
• Molecular Formula: C₂₀H₂₀FN₃O₆
• Molecular Weight: 417.394

Synonyms:1-(3-deoxy-3-fluoro-4,6-O-isopropylidene-β-D-glucopyranosyl-2-ulose)-N⁴-benzoylcytosine

Chemical Property of 1-(3-deoxy-3-fluoro-4,6-O-isopropylidene-β-D-glucopyranosyl-2-ulose)-N⁴-benzoylcytosine

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of 1-(3-deoxy-3-fluoro-4,6-O-isopropylidene-β-D-glucopyranosyl-2-ulose)-N⁴-benzoylcytosine

There total 5 articles about 1-(3-deoxy-3-fluoro-4,6-O-isopropylidene-β-D-glucopyranosyl-2-ulose)-N⁴-benzoylcytosine 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: 22.0%

1-(3-deoxy-3-fluoro-4,6-O-isopropylidene-β-D-glucopyranosyl)-N4-benzoyl cytosine (924279-87-8) → 1-(3-deoxy-3-fluoro-4,6-O-isopropylidene-β-D-glucopyranosyl-2-ulose)-N4-benzoylcytosine (924279-88-9)

Guidance literature:

With dipyridinium dichromate; acetic anhydride; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1016/j.bmc.2006.10.033

Reference yield:

1-(3-deoxy-3-fluoro-β-D-glucopyranosyl)-N4-benzoyl cytosine (924279-86-7) → 1-(3-deoxy-3-fluoro-4,6-O-isopropylidene-β-D-glucopyranosyl-2-ulose)-N4-benzoylcytosine (924279-88-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / p-toluenesulfonic acid / dimethylformamide / 1 h / 60 °C

2: 22 percent / pyridinium dichromate; acetic anhydride / CH₂Cl₂ / 3 h / 20 °C

With dipyridinium dichromate; acetic anhydride; toluene-4-sulfonic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2006.10.033

Reference yield:

1-(2,4,6-tri-O-acetyl-3-deoxy-3-fluoro-β-D-glucopyranosyl)-N4-benzoyl cytosine (924279-85-6) → 1-(3-deoxy-3-fluoro-4,6-O-isopropylidene-β-D-glucopyranosyl-2-ulose)-N4-benzoylcytosine (924279-88-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 3.31 g / pyridine; NaOH / ethanol / 0.5 h / 0 °C

2: 80 percent / p-toluenesulfonic acid / dimethylformamide / 1 h / 60 °C

3: 22 percent / pyridinium dichromate; acetic anhydride / CH₂Cl₂ / 3 h / 20 °C

With pyridine; sodium hydroxide; dipyridinium dichromate; acetic anhydride; toluene-4-sulfonic acid; In ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2006.10.033

upstream raw materials:

1-(3-deoxy-3-fluoro-4,6-O-isopropylidene-β-D-glucopyranosyl)-N⁴-benzoyl cytosine

1-(3-deoxy-3-fluoro-β-D-glucopyranosyl)-N⁴-benzoyl cytosine

1-(2,4,6-tri-O-acetyl-3-deoxy-3-fluoro-β-D-glucopyranosyl)-N⁴-benzoyl cytosine

[(2R,3R,4S,5S)-3,5,6-triacetoxy-4-fluoro-tetrahydropyran-2-yl]methyl acetate

Downstream raw materials:

N-[1-((2R,4S,5R,6R)-4-Fluoro-5-hydroxy-6-hydroxymethyl-3-oxo-tetrahydro-pyran-2-yl)-2-oxo-1,2-dihydro-pyrimidin-4-yl]-benzamide

1-(6-O-acetyl-3,4-dideoxy-3-fluoro-β-D-glycerohex-3-enopyranosyl-2-ulose)-N⁴-benzoylcytosine

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