5-fluoro-1-<5-O-(tert-butyldimethylsilyl)-2,3-dideoxy-2-fluoro-α-L-glycero-pent-2-enofuranosyl>-N⁴-benzoylcytosine

Base Information

• Chemical Name: 5-fluoro-1-<5-O-(tert-butyldimethylsilyl)-2,3-dideoxy-2-fluoro-α-L-glycero-pent-2-enofuranosyl>-N⁴-benzoylcytosine
• CAS No.: 221616-80-4
• Molecular Formula: C₂₂H₂₇F₂N₃O₄Si
• Molecular Weight: 463.556
• Mol file: 221616-80-4.mol

Synonyms:5-fluoro-1-<5-O-(tert-butyldimethylsilyl)-2,3-dideoxy-2-fluoro-α-L-glycero-pent-2-enofuranosyl>-N⁴-benzoylcytosine

Chemical Property of 5-fluoro-1-<5-O-(tert-butyldimethylsilyl)-2,3-dideoxy-2-fluoro-α-L-glycero-pent-2-enofuranosyl>-N⁴-benzoylcytosine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-fluoro-1-<5-O-(tert-butyldimethylsilyl)-2,3-dideoxy-2-fluoro-α-L-glycero-pent-2-enofuranosyl>-N⁴-benzoylcytosine

There total 5 articles about 5-fluoro-1-<5-O-(tert-butyldimethylsilyl)-2,3-dideoxy-2-fluoro-α-L-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:

tert-butyldimethylsilyl chloride (18162-48-6) → 5-fluoro-1-<5-O-(tert-butyldimethylsilyl)-2,3-dideoxy-2-fluoro-α-L-glycero-pent-2-enofuranosyl>-N4-benzoylcytosine (221616-80-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) conc. HCl, 2.) imidazole / 1.) EtOH, RT, 2 h, 2.) CH₂Cl₂, RT, 4 h

2: DIBAL-H / CH₂Cl₂ / 2 h / -78 °C

3: Et₃N / CH₂Cl₂ / 2 h / Ambient temperature

4: 1.) hexamethyldisilazane, ammonium sulfate, 2.) TMSOTf / 1.) reflux, 3 h, 2.) 1,2-dichloroethane, RT, 1 h

With 1H-imidazole; hydrogenchloride; ammonium sulfate; trimethylsilyl trifluoromethanesulfonate; diisobutylaluminium hydride; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; In dichloromethane;

DOI:10.1021/jm980651u

Reference yield:

(R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-3-fluoro-2,5-dihydro-furan-2-ol (221616-72-4) → 5-fluoro-1-<5-O-(tert-butyldimethylsilyl)-2,3-dideoxy-2-fluoro-α-L-glycero-pent-2-enofuranosyl>-N4-benzoylcytosine (221616-80-4)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N / CH₂Cl₂ / 2 h / Ambient temperature

2: 1.) hexamethyldisilazane, ammonium sulfate, 2.) TMSOTf / 1.) reflux, 3 h, 2.) 1,2-dichloroethane, RT, 1 h

With ammonium sulfate; trimethylsilyl trifluoromethanesulfonate; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; In dichloromethane;

DOI:10.1021/jm980651u

Reference yield:

(E)/(Z)-ethyl 3-<(R)-2,2-dimethyl-1,3-dioxolan-4-yl>-2-fluoroacrylate (221616-69-9) → 5-fluoro-1-<5-O-(tert-butyldimethylsilyl)-2,3-dideoxy-2-fluoro-α-L-glycero-pent-2-enofuranosyl>-N4-benzoylcytosine (221616-80-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) conc. HCl, 2.) imidazole / 1.) EtOH, RT, 2 h, 2.) CH₂Cl₂, RT, 4 h

2: DIBAL-H / CH₂Cl₂ / 2 h / -78 °C

3: Et₃N / CH₂Cl₂ / 2 h / Ambient temperature

4: 1.) hexamethyldisilazane, ammonium sulfate, 2.) TMSOTf / 1.) reflux, 3 h, 2.) 1,2-dichloroethane, RT, 1 h

With 1H-imidazole; hydrogenchloride; ammonium sulfate; trimethylsilyl trifluoromethanesulfonate; diisobutylaluminium hydride; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; In dichloromethane;

DOI:10.1021/jm980651u

upstream raw materials:

N-benzoyl-5-fluorocytosine

1-acetyl-4-<(tert-butyldimethylsilyloxy)methyl>-2-fluoro-2-buten-4-olide

tert-butyldimethylsilyl chloride

(E)/(Z)-ethyl 3-<(R)-2,2-dimethyl-1,3-dioxolan-4-yl>-2-fluoroacrylate

Downstream raw materials:

5-fluoro-1-(2,3-dideoxy-2-fluoro-α-L-glycero-pent-2-enofuranosyl)cytosine

5-fluoro-1-(2,3-dideoxy-2-fluoro-α-L-glycero-pent-2-enofuranosyl)-N⁴-benzoylcytosine

Refernces