Regiochemistry of epoxide ring opening in methyl 2,3-anhydro-4-azido-4-deoxy-α- and β- l-lyxopyranosides

• Published in: Carbohydrate research Vol. 340; no. 11; pp. 1866 - 1871
• Main Authors: Popsavin, Velimir, Benedeković, Goran, Popsavin, Mirjana, Srećo, Bojana, Djoković, Dejan
• Format: Journal Article
• Language: English
• Published: Netherlands Elsevier Ltd 15.08.2005
• Subjects: 2,3-Anhydro-lyxopyranosides; 2,3-Anhydro-ribopyranosides; Arabinose - chemistry; Azides - chemistry; Azido sugars; Carbohydrate Conformation; Chromatography, Thin Layer; Epoxide ring opening; Epoxy Compounds - chemistry; Glycosides - chemistry; Magnetic Resonance Spectroscopy; Models, Chemical; Regioselectivity; Spectrophotometry, Infrared; Temperature; 2,3-Anhydro-lyxopyranosides; Azido sugars; Epoxide ring opening; Regioselectivity; 2,3-Anhydro-ribopyranosides

[Display omitted] Methyl 2,3-anhydro-4- O-methanesulfonyl-α- 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...