title: Synthesis of tri-O-acetyl-D-allal from levoglucosenone.
abstract: Tri-O-acetyl-D-allal has been enantiospecifically synthesized in six steps from levoglucosenone in 55% overall yield. A key step in the synthesis is the anhydro bridge ring-opening with concomitant formation of a 1,3-oxathiolane-2-thione ring.
authors.affiliation: Instituto de Química Rosario, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario, CONICET Suipacha 531, S2002LRK Rosario, Argentina.
authors.forename: Enrique D V
authors.initials: ED
authors.lastname: Giordano
authors.forename: Agustina
authors.initials: A
authors.lastname: Frinchaboy
authors.forename: Alejandra G
authors.initials: AG
authors.lastname: Suárez
authors.forename: Rolando A
authors.initials: RA
authors.lastname: Spanevello
mesh_terms: D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry*; D005947:Glucose / Q000031:analogs & derivatives* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure
chemical_list: C579144:1,5-anhydro-2-deoxy-D-ribo-hex-1-enitol; D019086:Bridged Bicyclo Compounds, Heterocyclic; C512757:1,6-anhydro-3,4-dideoxyhex-3-enopyran-2-ulose; D005947:Glucose