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.
Popsavin
Velimir
V
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
Benedeković
Goran
G
Popsavin
Mirjana
M
Srećo
Bojana
B
Djoković
Dejan
D
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