Synthetic Use Of Epoxy-Sugar Nucleosides

Abstract

Preparation of 1′,2 ′-, 3 ′,4 ′-, and 4 ′,5 ′-epoxy derivatives of nucleosides and their use for the stereoselective synthesis of 1′- and 4 ′-branched analogues are described.

Keywords:

• Unsaturated-sugar nucleoside
• dimethyl dioxirane
• epoxy-sugar nucleoside
• organoaluminum reagent
• ring opening
• branched-sugar nucleoside
• anti-HIV activity

Acknowledgments

The present studies were supported by grants from the Japan Health Science Foundation (SA14804 to H.T.) and Grant-in-Aid (KAKENHI) from Japan Society for the Promotion of Science (No. 17590093 to H.K. and No. 17590094 to H.T.). Anti-HIV-1 activity of the 4′-carbon-substituted d4T analogues synthesized in our study was evaluated by Professor Yung-Chi Cheng (Yale University) and Professor Masanori Baba (Kagoshima University).