Regiochemistry of epoxide ring opening in methyl 2,3-anhydro-4-azido-4-deoxy-alpha- and beta-L-lyxopyranosides.
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.
Department of Chemistry, Faculty of Sciences, University of Novi Sad, Trg D. Obradovića 3, 21000 Novi Sad, Serbia and Montenegro. popsavin@ih.ns.ac.yu
Velimir
V
Popsavin
Goran
G
Benedeković
Mirjana
M
Popsavin
Bojana
B
Srećo
Dejan
D
Djoković
D001089:Arabinose / Q000737:chemistry*; D001386:Azides / Q000737:chemistry; D002236:Carbohydrate Conformation; D002855:Chromatography, Thin Layer; D004852:Epoxy Compounds / Q000737:chemistry*; D006027:Glycosides / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D013055:Spectrophotometry, Infrared; D013696:Temperature
D001386:Azides; D004852:Epoxy Compounds; D006027:Glycosides; D001089:Arabinose