An Alternative Pathway to Ribonucleoside 尾-Hydroxyphosphonate Analogues and Related Prodrugs

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• 作者：Audrey Hospital ; Ma茂a Meurillon ; Suzanne Peyrottes ; Christian P茅rigaud
• 刊名：Organic Letters
• 出版年：2013
• 出版时间：September 20, 2013
• 年：2013
• 卷：15
• 期：18
• 页码：4778-4781
• 全文大小：297K
• 年卷期：v.15,no.18(September 20, 2013)
• ISSN：1523-7052

文摘

Nucleoside 尾-(S)-hydroxyphosphonate analogues have recently proven to be interesting bioactive compounds as 5鈥?nucleotidase inhibitors. These derivatives were obtained in a pyrimidine series through an ex-chiral pool pathway or the stereoselective reduction of a 尾-ketophosphonate intermediate. Herein, an original synthesis of these compounds using nucleoside epoxide intermediates, containing either a pyrimidine or a purine as nucleobase, was explored and allowed the direct synthesis of the corresponding bis S-acyl-2-thioethyl (SATE) prodrugs.