N⁴-benzoyl-5-fluoro-1-[(1R,3S,5S,7R,8R)-8-hydroxy-7-(hydroxymethyl)-5-phenyl-2,6-dioxabicyclo[3.3.0]octan-3-yl]cytosine

Base Information

• Chemical Name: N⁴-benzoyl-5-fluoro-1-[(1R,3S,5S,7R,8R)-8-hydroxy-7-(hydroxymethyl)-5-phenyl-2,6-dioxabicyclo[3.3.0]octan-3-yl]cytosine
• CAS No.: 881423-91-2
• Molecular Formula: C₂₄H₂₂FN₃O₆
• Molecular Weight: 467.454

Synonyms:N⁴-benzoyl-5-fluoro-1-[(1R,3S,5S,7R,8R)-8-hydroxy-7-(hydroxymethyl)-5-phenyl-2,6-dioxabicyclo[3.3.0]octan-3-yl]cytosine

Chemical Property of N⁴-benzoyl-5-fluoro-1-[(1R,3S,5S,7R,8R)-8-hydroxy-7-(hydroxymethyl)-5-phenyl-2,6-dioxabicyclo[3.3.0]octan-3-yl]cytosine

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

Technology Process of N⁴-benzoyl-5-fluoro-1-[(1R,3S,5S,7R,8R)-8-hydroxy-7-(hydroxymethyl)-5-phenyl-2,6-dioxabicyclo[3.3.0]octan-3-yl]cytosine

There total 4 articles about N⁴-benzoyl-5-fluoro-1-[(1R,3S,5S,7R,8R)-8-hydroxy-7-(hydroxymethyl)-5-phenyl-2,6-dioxabicyclo[3.3.0]octan-3-yl]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:

Acetic acid (2R,3R,3aR,5S,6aS)-5-(4-benzoylamino-5-fluoro-2-oxo-2H-pyrimidin-1-yl)-2-hydroxymethyl-6a-phenyl-hexahydro-furo[3,2-b]furan-3-yl ester → N4-benzoyl-5-fluoro-1-[(1R,3S,5S,7R,8R)-8-hydroxy-7-(hydroxymethyl)-5-phenyl-2,6-dioxabicyclo[3.3.0]octan-3-yl]cytosine (881423-91-2)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; methanol; water; at 0 ℃;

DOI:10.1021/jo052413u

Reference yield:

1-{(1S,3R,4R,5R,7S)-4-acetoxy-3-[(tert-butyldiphenylsilyloxy)methyl]-1-phenyl-2,6-dioxabicyclo[3.3.0]octan-7-yl}-N4-benzoyl-5-fluorocytosine (881423-90-1) → N4-benzoyl-5-fluoro-1-[(1R,3S,5S,7R,8R)-8-hydroxy-7-(hydroxymethyl)-5-phenyl-2,6-dioxabicyclo[3.3.0]octan-3-yl]cytosine (881423-91-2)

Guidance literature:

Multi-step reaction with 2 steps

1: TBAF / tetrahydrofuran / 20 °C

2: NaOH / tetrahydrofuran; methanol; H₂O / 0 °C

With sodium hydroxide; tetrabutyl ammonium fluoride; In tetrahydrofuran; methanol; water;

DOI:10.1021/jo052413u

Reference yield:

N-benzoyl-5-fluorocytosine (10357-07-0) → N4-benzoyl-5-fluoro-1-[(1R,3S,5S,7R,8R)-8-hydroxy-7-(hydroxymethyl)-5-phenyl-2,6-dioxabicyclo[3.3.0]octan-3-yl]cytosine (881423-91-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 33 percent / trimethylsilyl N-(trimethylsilyl)acetimidate; TMSOTf / acetonitrile / 1 h

2: TBAF / tetrahydrofuran / 20 °C

3: NaOH / tetrahydrofuran; methanol; H₂O / 0 °C

With sodium hydroxide; N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; In tetrahydrofuran; methanol; water; acetonitrile;

DOI:10.1021/jo052413u

upstream raw materials:

1-{(1S,3R,4R,5R,7S)-4-acetoxy-3-[(tert-butyldiphenylsilyloxy)methyl]-1-phenyl-2,6-dioxabicyclo[3.3.0]octan-7-yl}-N⁴-benzoyl-5-fluorocytosine

N-benzoyl-5-fluorocytosine

(1R,3R,4R,5R,7RS)-1-phenyl-3-(tert-butyldiphenylsilyloxymethyl)-4,7-diacetoxy-2,6-dioxabicylco[3.3.0]octane

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