Development of a Novel Synthetic Process for 2-Deoxy-3,5-di-O-p-toluoyl--L-ribofuranosyl Chlori
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- 作者：Narayan C. Chaudhuri ; Adel Moussa ; Alistair Stewart ; Jingyang Wang ; and Richard Storer
- 刊名：Organic Process Research & Development
- 出版年：2005
- 出版时间：July 2005
- 年：2005
- 卷：9
- 期：4
- 页码：457 - 465
- 全文大小：123K
- 年卷期：v.9,no.4(July 2005)
- ISSN：1520-586X
文摘
A novel synthetic route to 2-deoxy-3,5-di-O-p-toluoyl-
-L-ribofuranosyl chloride (1) from inexpensive D-xylose (3) isdescribed. 1 is a key intermediate in the synthesis of the antiviralagent 1-(2-deoxy-
-L-ribofuranosyl)thymine (-L-thymidine) (2)and other 2'-deoxy-L-ribonucleosides. This seven-step synthesisemploys a key conversion of the D to the L configuration of thesugar moiety (6 to 7 in Scheme 1) using simple reagents andreaction conditions. The entire process involves only threeisolation steps. The key compound (1) was produced in 11%overall yield without chromatography.
-L-ribofuranosyl chloride (1) from inexpensive D-xylose (3) isdescribed. 1 is a key intermediate in the synthesis of the antiviralagent 1-(2-deoxy--L-ribofuranosyl)thymine (-L-thymidine) (2)and other 2'-deoxy-L-ribonucleosides. This seven-step synthesisemploys a key conversion of the D to the L configuration of thesugar moiety (6 to 7 in Scheme 1) using simple reagents andreaction conditions. The entire process involves only threeisolation steps. The key compound (1) was produced in 11%overall yield without chromatography.