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

Base Information

• Chemical Name: 1-(3-deoxy-3-fluoro-4,6-O-isopropylidene-β-D-glucopyranosyl)-N⁴-benzoyl cytosine
• CAS No.: 924279-87-8
• Molecular Formula: C₂₀H₂₂FN₃O₆
• Molecular Weight: 419.41

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

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

Chemical Property:

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

There total 4 articles about 1-(3-deoxy-3-fluoro-4,6-O-isopropylidene-β-D-glucopyranosyl)-N⁴-benzoyl 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: 80.0%

1-(3-deoxy-3-fluoro-β-D-glucopyranosyl)-N4-benzoyl cytosine (924279-86-7) + 2,2-dimethoxy-propane (77-76-9) → 1-(3-deoxy-3-fluoro-4,6-O-isopropylidene-β-D-glucopyranosyl)-N4-benzoyl cytosine (924279-87-8)

Guidance literature:

With toluene-4-sulfonic acid; In N,N-dimethyl-formamide; at 60 ℃; for 1h;

DOI:10.1016/j.bmc.2006.10.033 DOI:10.1016/j.ejmech.2007.04.001

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)-N4-benzoyl cytosine (924279-87-8)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With pyridine; sodium hydroxide; toluene-4-sulfonic acid; In ethanol; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2006.10.033

Reference yield:

[(2R,3R,4S,5S)-3,5,6-triacetoxy-4-fluoro-tetrahydropyran-2-yl]methyl acetate (7226-43-9,20409-32-9,22434-91-9,22434-92-0,88198-26-9,83602-93-1) → 1-(3-deoxy-3-fluoro-4,6-O-isopropylidene-β-D-glucopyranosyl)-N4-benzoyl cytosine (924279-87-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 68 percent / hexamethyldisilazane; saccharine; trimethylsilyl trifluoromethanesulfonate / acetonitrile / 5 h / 120 °C

2: 3.31 g / pyridine; NaOH / ethanol / 0.5 h / 0 °C

3: 80 percent / p-toluenesulfonic acid / dimethylformamide / 1 h / 60 °C

With pyridine; sodium hydroxide; trimethylsilyl trifluoromethanesulfonate; toluene-4-sulfonic acid; 1,1,1,3,3,3-hexamethyl-disilazane; saccharin; In ethanol; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/j.bmc.2006.10.033

upstream raw materials:

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

2,2-dimethoxy-propane

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:

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

1-(3-deoxy-3-fluoro-4,6-O-isopropylidene-2-O-phenoxythiocarbonyl-β-D-glucopyranosyl)-N(4)-benzoyl cytosine

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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