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

Base Information

• Chemical Name: 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
• CAS No.: 881423-90-1
• Molecular Formula: C₄₂H₄₂FN₃O₇Si
• Molecular Weight: 747.895

Synonyms: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

Chemical Property of 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

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Technology Process of 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

There total 1 articles about 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 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: 33.0%

N-benzoyl-5-fluorocytosine (10357-07-0) + (1R,3R,4R,5R,7RS)-1-phenyl-3-(tert-butyldiphenylsilyloxymethyl)-4,7-diacetoxy-2,6-dioxabicylco[3.3.0]octane (389633-40-3) → acetic acid 5-(4-benzoylamino-5-fluoro-2-oxo-2H-pyrimidin-1-yl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-6a-phenyl-hexahydro-furo[3,2-b]furan-3-yl ester + 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)

Guidance literature:

With N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; In acetonitrile; for 1h;

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) → 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

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃;

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) → N-(1-{(2S,3aS,5R,6R,6aR)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-6-hydroxy-3a-phenyl-hexahydro-furo[3,2-b]furan-2-yl}-5-fluoro-2-oxo-1,2-dihydro-pyrimidin-4-yl)-benzamide

Guidance literature:

Multi-step reaction with 3 steps

1: TBAF / tetrahydrofuran / 20 °C

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

3: pyridine / 1 h

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

DOI:10.1021/jo052413u

upstream raw materials:

N-benzoyl-5-fluorocytosine

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

Downstream raw materials:

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

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