Regiochemistry of epoxide ring opening in methyl 2,3-anhydro-4-azido-4-deoxy-alpha- and beta-L-lyxopyranosides

Velimir Popsavin; Goran Benedeković; Mirjana Popsavin; Bojana Srećo; Dejan Djoković

doi:10.1016/j.carres.2005.06.006

Regiochemistry of epoxide ring opening in methyl 2,3-anhydro-4-azido-4-deoxy-alpha- and beta-L-lyxopyranosides

Carbohydr Res. 2005 Aug 15;340(11):1866-71. doi: 10.1016/j.carres.2005.06.006.

Authors

Velimir Popsavin¹, Goran Benedeković, Mirjana Popsavin, Bojana Srećo, Dejan Djoković

Affiliation

¹ 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

PMID: 15992785
DOI: 10.1016/j.carres.2005.06.006

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Arabinose / chemistry*
Azides / chemistry
Carbohydrate Conformation
Chromatography, Thin Layer
Epoxy Compounds / chemistry*
Glycosides / chemistry
Magnetic Resonance Spectroscopy
Models, Chemical
Spectrophotometry, Infrared
Temperature

Substances

Azides
Epoxy Compounds
Glycosides
Arabinose