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Regiochemistry of epoxide ring opening in methyl 2,3-anhydro-4-azido-4-deoxy-alpha- and beta-L-lyxopyranosides |
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| Authors: | Popsavin Velimir Benedeković Goran Popsavin Mirjana Srećo Bojana Djoković Dejan |
| Institution: | Department of Chemistry, Faculty of Sciences, University of Novi Sad, Trg D. Obradovi?a 3, 21000 Novi Sad, Serbia and Montenegro. popsavin@ih.ns.ac.yu |
| Abstract: | Methyl 2,3-anhydro-4-O-methanesulfonyl-alpha-d-ribopyranoside (12) was prepared through a new six-step sequence starting from d-arabinose. Chemical behaviour of 12 was further studied under solvolytic conditions and in the presence of azide anion as a nucleophile. Factors governing the regiochemistry of epoxide ring opening are briefly discussed. |
| Keywords: | 2 3-Anhydro-ribopyranosides 2 3-Anhydro-lyxopyranosides Epoxide ring opening Regioselectivity Azido sugars |
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