Synthesis and conformational studies on methyl 4-O-acetyl-3-azido-2,3,6-trideoxy-hex-5-enopyranosides of the L series.
Methyl 3-azido-2,3-dideoxy-alpha-D-xylo-, -alpha-D-lyxo-, and -beta-D-xylo-hexopyranosides were converted into 4-O-acetyl-3-azido-6-iodo-2,3,6-trideoxy analogues via 6-O-p-tolylsulfonyl compounds. The elimination of hydrogen iodide from 6-iodo glycosides yielded methyl 4-O-acetyl-3-azido-2,3,6-trideoxy-beta-L-erythro-, -alpha-L-threo-, and -beta-L-threo-hex-5-enopyranosides. The configuration and conformation of all products are evaluated in depth on the basis of (1)H and (13)C NMR data. Factors determining conformational energy in 4-O-protected-3-azido-2,3,6,-trideoxy-hex-5-enopyranosides are discussed.
Liberek
Beata
B
Faculty of Chemistry, University of Gdańsk, Sobieskiego 18, PL-80-952 Gdańsk, Poland. beatal@chem.univ.gda.pl
D000107:Acetylation; D001386:Azides / Q000138:chemical synthesis* / Q000737:chemistry; D002236:Carbohydrate Conformation; D003837:Deoxy Sugars / Q000138:chemical synthesis* / Q000737:chemistry*; D019906:Nuclear Magnetic Resonance, Biomolecular; D014105:Tosyl Compounds / Q000138:chemical synthesis
D001386:Azides; D003837:Deoxy Sugars; D014105:Tosyl Compounds