1-[5-O-(t-butyldiphenylsilyl)-α-L-lyxofuranosyl]-5-fluorocytosine

Base Information

• Chemical Name: 1-[5-O-(t-butyldiphenylsilyl)-α-L-lyxofuranosyl]-5-fluorocytosine
• CAS No.: 1382683-45-5
• Molecular Formula: C₂₅H₃₀FN₃O₅Si
• Molecular Weight: 499.614
• Mol file: 1382683-45-5.mol

Synonyms:1-[5-O-(t-butyldiphenylsilyl)-α-L-lyxofuranosyl]-5-fluorocytosine

Chemical Property of 1-[5-O-(t-butyldiphenylsilyl)-α-L-lyxofuranosyl]-5-fluorocytosine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[5-O-(t-butyldiphenylsilyl)-α-L-lyxofuranosyl]-5-fluorocytosine

There total 5 articles about 1-[5-O-(t-butyldiphenylsilyl)-α-L-lyxofuranosyl]-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: 86.0%

1-(α-L-Lyxofuranosyl)-5-fluorocytosine (1382683-43-3) + tert-butylchlorodiphenylsilane (58479-61-1) → 1-[5-O-(t-butyldiphenylsilyl)-α-L-lyxofuranosyl]-5-fluorocytosine (1382683-45-5)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; Cooling with ice;

DOI:10.1080/00397911.2011.571805

Reference yield:

methyl L-lyxofuranoside (202119-57-1) → 1-[5-O-(t-butyldiphenylsilyl)-α-L-lyxofuranosyl]-5-fluorocytosine (1382683-45-5)

Guidance literature:

Multi-step reaction with 5 steps

1: pyridine / 20 °C / Cooling with ice

2: sulfuric acid / acetic acid / 5 h / 20 °C / Cooling with ice

3: trimethylsilyl trifluoromethanesulfonate / dichloromethane / Cooling with ice; Reflux

4: ammonia / methanol / 5 h / 20 °C

5: 1H-imidazole / N,N-dimethyl-formamide / 20 °C / Cooling with ice

With pyridine; 1H-imidazole; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; ammonia; In methanol; dichloromethane; acetic acid; N,N-dimethyl-formamide;

DOI:10.1080/00397911.2011.571805

Reference yield:

L-lyxofuranose (532-20-7,613-83-2,7261-25-8,7687-39-0,13221-22-2,14795-83-6,15761-67-8,20074-49-1,25545-03-3,25545-04-4,32445-75-3,36441-93-7,36468-53-8,37110-85-3,37388-49-1,38029-69-5,40461-77-6,40461-89-0,41546-19-4,41546-20-7,41546-21-8,41546-26-3,41546-29-6,41546-30-9,41546-31-0,126872-16-0,131064-98-7,34436-17-4) → 1-[5-O-(t-butyldiphenylsilyl)-α-L-lyxofuranosyl]-5-fluorocytosine (1382683-45-5)

Guidance literature:

Multi-step reaction with 6 steps

1: sulfuric acid / 5 h / 20 °C / Cooling with ice

2: pyridine / 20 °C / Cooling with ice

3: sulfuric acid / acetic acid / 5 h / 20 °C / Cooling with ice

4: trimethylsilyl trifluoromethanesulfonate / dichloromethane / Cooling with ice; Reflux

5: ammonia / methanol / 5 h / 20 °C

6: 1H-imidazole / N,N-dimethyl-formamide / 20 °C / Cooling with ice

With pyridine; 1H-imidazole; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; ammonia; In methanol; dichloromethane; acetic acid; N,N-dimethyl-formamide;

DOI:10.1080/00397911.2011.571805

upstream raw materials:

1-(2,3,5-tri-O-acetyl-α-L-lyxofuranosyl)-5-fluorocytosine

1-(α-L-Lyxofuranosyl)-5-fluorocytosine

tert-butylchlorodiphenylsilane

L-lyxofuranose

Downstream raw materials:

1-{5-O-t-butyldiphenylsilyl-2,3-di-O-[methylthio(thiocarbonyl)]-α-L-lyxofuranosyl}-5-fluorocytosine

2',3'-dideoxy-5-fluoro-5'-O-(tbutyldiphenylsilyl)-α-L-cytidine

α-elvucitabine