5-methyl-1-[5-O-(tert-butyldimethylsilyl)-2,3-dideoxy-2-fluoro-β-D-glycero-pent-2-enofuranosyl]-N⁴-benzoylcytosine

Base Information

• Chemical Name: 5-methyl-1-[5-O-(tert-butyldimethylsilyl)-2,3-dideoxy-2-fluoro-β-D-glycero-pent-2-enofuranosyl]-N⁴-benzoylcytosine
• CAS No.: 405238-89-3
• Molecular Formula: C₂₃H₃₀FN₃O₄Si
• Molecular Weight: 459.593

Synonyms:5-methyl-1-[5-O-(tert-butyldimethylsilyl)-2,3-dideoxy-2-fluoro-β-D-glycero-pent-2-enofuranosyl]-N⁴-benzoylcytosine

Chemical Property of 5-methyl-1-[5-O-(tert-butyldimethylsilyl)-2,3-dideoxy-2-fluoro-β-D-glycero-pent-2-enofuranosyl]-N⁴-benzoylcytosine

Chemical Property:

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Technology Process of 5-methyl-1-[5-O-(tert-butyldimethylsilyl)-2,3-dideoxy-2-fluoro-β-D-glycero-pent-2-enofuranosyl]-N⁴-benzoylcytosine

There total 5 articles about 5-methyl-1-[5-O-(tert-butyldimethylsilyl)-2,3-dideoxy-2-fluoro-β-D-glycero-pent-2-enofuranosyl]-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: 43.2%

1-acetyl-4-[(tert-butyldimethylsilyloxy)methyl]-2-fluoro-2-buten-4-olide (405238-68-8) + N-(5-methyl-2-oxo-1-trimethylsilanyl-1,2-dihydro-pyrimidin-4-yl)-benzamide (1005770-60-4) → 5-methyl-1-[5-O-(tert-butyldimethylsilyl)-2,3-dideoxy-2-fluoro-β-D-glycero-pent-2-enofuranosyl]-N4-benzoylcytosine (405238-89-3) + 5-methyl-1-[5-O-(tert-butyldimethylsilyl)-2,3-dideoxy-2-fluoro-α-D-glycero-pent-2-enofuranosyl]-N4-benzoylcytosine (405238-90-6)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In 1,2-dichloro-ethane; at 20 ℃; for 5h;

DOI:10.1021/jm010418n

Reference yield:

(E)/(Z)-ethyl 3-[(S)-2,2-dimethyl-(1,3)-dioxolan-4-yl]-2-fluoroacrylate (147410-74-0) → 5-methyl-1-[5-O-(tert-butyldimethylsilyl)-2,3-dideoxy-2-fluoro-β-D-glycero-pent-2-enofuranosyl]-N4-benzoylcytosine (405238-89-3)

Guidance literature:

Multi-step reaction with 5 steps

1: conc. aq. HCl / ethanol / 2.5 h / 20 °C

2: imidazole / CH₂Cl₂ / 20 °C

3: DIBAL-H / CH₂Cl₂ / 2 h / -78 °C

4: 4.79 g / Et₃N / CH₂Cl₂ / 2 h / 20 °C

5: 43.2 percent / TMSOTf / 1,2-dichloro-ethane / 5 h / 20 °C

With 1H-imidazole; hydrogenchloride; trimethylsilyl trifluoromethanesulfonate; diisobutylaluminium hydride; triethylamine; In ethanol; dichloromethane; 1,2-dichloro-ethane;

DOI:10.1021/jm010418n

Reference yield:

(S)-(-)-2-Fluoro-4-(hydroxymethyl)-2-buten-4-olide (154540-16-6) → 5-methyl-1-[5-O-(tert-butyldimethylsilyl)-2,3-dideoxy-2-fluoro-β-D-glycero-pent-2-enofuranosyl]-N4-benzoylcytosine (405238-89-3)

Guidance literature:

Multi-step reaction with 4 steps

1: imidazole / CH₂Cl₂ / 20 °C

2: DIBAL-H / CH₂Cl₂ / 2 h / -78 °C

3: 4.79 g / Et₃N / CH₂Cl₂ / 2 h / 20 °C

4: 43.2 percent / TMSOTf / 1,2-dichloro-ethane / 5 h / 20 °C

With 1H-imidazole; trimethylsilyl trifluoromethanesulfonate; diisobutylaluminium hydride; triethylamine; In dichloromethane; 1,2-dichloro-ethane;

DOI:10.1021/jm010418n

upstream raw materials:

1-acetyl-4-[(tert-butyldimethylsilyloxy)methyl]-2-fluoro-2-buten-4-olide

N-(5-methyl-2-oxo-1-trimethylsilanyl-1,2-dihydro-pyrimidin-4-yl)-benzamide

(E)/(Z)-ethyl 3-[(S)-2,2-dimethyl-(1,3)-dioxolan-4-yl]-2-fluoroacrylate

(S)-(-)-2-Fluoro-4-(hydroxymethyl)-2-buten-4-olide

Downstream raw materials:

N-[1-((2R,5S)-3-Fluoro-5-hydroxymethyl-2,5-dihydro-furan-2-yl)-5-methyl-2-oxo-1,2-dihydro-pyrimidin-4-yl]-benzamide

5-methyl-1-(2,3-dideoxy-2-fluoro-β-D-glycero-pent-2-enofuranosyl)cytosine

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