title: Cyanohydrins from methyl 6-deoxy-2,3-O-isopropylidene-α-l-lyxo-hexofuranosid-4-ulose via Bucherer-Bergs and Strecker reactions.
abstract: The formation of methyl 4-cyano-6-deoxy-2,3-O-isopropylidene-α-l-talopyranoside (3), methyl 4-cyano-6-deoxy-2,3-O-isopropylidene-α-l-mannopyranoside (4), methyl 4-cyano-6-deoxy-2,3-O-isopropylidene-β-d-allopyranoside (5), and methyl 4-cyano-6-deoxy-2,3-O-isopropylidene-β-d-gulopyranoside (7) from methyl 6-deoxy-2,3-O-isopropylidene-α-l-lyxo-hexopyranosid-4-ulose (1) under Strecker amino nitrile synthesis and Bucherer-Bergs hydantoin synthesis reaction conditions, respectively, is reported. Their structures were determined on the basis of NMR and mass spectral data. The configurations of free cyanohydrins 3 and 4 and 4-O-acetylated cyanohydrins 6 and 8 (obtained by acetylation of 5 and 7, respectively) were established by single-crystal X-ray analysis. The conformations of the six-membered pyranose ring and five-membered 1,3-dioxolane ring in compounds 3, 4, 6, and 8 are also reported.
authors: Institute of Chemistry, Centre of Excellence GLYCOMED, Slovak Academy of Sciences, Dúbravská cesta 9, SK-845 38 Bratislava, Slovakia.
authors: Bohumil
authors: B
authors: Steiner
authors: Vratislav
authors: V
authors: Langer
authors: Maroš
authors: M
authors: Bella
authors: Miroslav
authors: M
authors: Koóš
mesh_terms: D018360:Crystallography, X-Ray; D015394:Molecular Structure; D009005:Monosaccharides / Q000737:chemistry*; D009570:Nitriles / Q000737:chemistry*
chemical_list: D009005:Monosaccharides; D009570:Nitriles; C430593:cyanohydrin