title: Synthesis of chiral β-iodo- and vinylorganophosphorus(V) compounds by fragmentation of carbohydrate anomeric alkoxyl radicals.
abstract: A new general methodology for the synthesis of chiral vinylphosphonate and vinylphosphine oxide carbohydrate derivatives has been developed using the anomeric alkoxyl radical fragmentation reaction as the key step. The synthetic sequence proceeded via β-iodophosphonate and β-iodophosphine oxide intermediates, which may be interesting synthons for the introduction of phosphorus into organic molecules. These vinylphosphonates could be easily transformed into 2-methylene-1-phosphapentofuranoses (3-methylene-1,2-oxaphospholanes) and β-aminophosphonates, isosteres of biologically active α-methylene-γ-lactones and β-amino acids, respectively.
authors.affiliation: Instituto de Productos Naturales y Agrobiología del CSIC, Carretera de La Esperanza 3, 38206 La Laguna, Tenerife, Spain.
authors.forename: Daniel
authors.initials: D
authors.lastname: Hernández-Guerra
authors.forename: María S
authors.initials: MS
authors.lastname: Rodríguez
authors.forename: Ernesto
authors.initials: E
authors.lastname: Suárez
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D000596:Amino Acids / Q000737:chemistry; D002241:Carbohydrates / Q000138:chemical synthesis* / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D006847:Hydrocarbons, Iodinated / Q000737:chemistry*; D015394:Molecular Structure; D009943:Organophosphorus Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013402:Sugar Alcohols / Q000138:chemical synthesis; D014753:Vinyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000438:Alcohols; D000596:Amino Acids; D002241:Carbohydrates; D006847:Hydrocarbons, Iodinated; D009943:Organophosphorus Compounds; D013402:Sugar Alcohols; D014753:Vinyl Compounds; C059688:alkoxyl radical