• 10.1021/jm960098l
  • Journal of Medicinal Chemistry
  • Volume 39
  • January 1996
  • pp 2835-2843

Structure−Activity Relationships of 1-(2-Deoxy-2-fluoro-β- l -arabino- furanosyl)pyrimidine Nucleosides as Anti-Hepatitis B Virus Agents

reproducible synthesis process


Synthesized (10) on beach in the lab and also pilot plant when I was working in company. The synthesis procedue is reproducible even in a 5 L scale reaction in the lab. 

The starting material L-Xylose canot be abtained from natural substances which results a very high cost of manufacturing in the plant. So I modified the reaction to synthesis (7)  following the patent PCT US9815375 started with L-arabinose, resulting a much less cost. 

The procedue for (10) is not usable for manufacturing in the plant because of high toxicity of HF and low controllability. I synthesized Pyridin-HF salt which is a oil like liquid as F source for this reaction which give a 100% yield. 

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