Synthesis of Seven-Membered Ring Nucleosides and Serendipitous Simmons-Smith O-Glycosylation
Sunit Kumar Jana1, Masad J Damha1
1Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, QC, Canada H3A 0B8.
Abstract:
A series of seven-membered (oxepine) nucleosides containing various nucleobases (A, U, T, 5-FU, C) were synthesized by ring expansion of cyclopropanated glucals. We expect this new series of ring-expanded nucleic acid analogues to be useful as building blocks in the design of mixed base functional genetic systems. While exploring alternative pathways to oxepine nucleoside synthesis, we discovered an unprecedented α-stereoselective O-glycosylation of 1,2-glucals under mild Simmons-Smith conditions.
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