title: Synthesis of carbohydrate-based vinyl selenides via Wittig-type reactions.
abstract: Carbohydrate-based vinyl selenides of the arabino, ribo and 2-deoxy-ribo configuration have been prepared by Wittig-type reactions of various protected furanoses. Moderate yields were always obtained due to the nature and reactivity of both carbohydrate lactols and selenium-based olefinating reagents under the conditions tested. A detailed study of the olefination reaction and the behaviour of vinyl selenides towards the electrophilic-induced cyclization will be discussed.
authors.affiliation: Departament de Química Analítica i Química Orgànica, Facultat de Química, Universitat Rovira i Virgili, c/o Marcel.lí Domingo s/n, E-43007 Tarragona, Spain.
authors.forename: Omar
authors.initials: O
authors.lastname: Boutureira
authors.forename: M Isabel
authors.initials: MI
authors.lastname: Matheu
authors.forename: Yolanda
authors.initials: Y
authors.lastname: Díaz
authors.forename: Sergio
authors.initials: S
authors.lastname: Castillón
mesh_terms: D001089:Arabinose / Q000737:chemistry; D002241:Carbohydrates / Q000138:chemical synthesis* / Q000737:chemistry; D003837:Deoxy Sugars / Q000737:chemistry; D016566:Organoselenium Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013402:Sugar Alcohols / Q000737:chemistry; D014753:Vinyl Compounds / Q000737:chemistry*
chemical_list: D002241:Carbohydrates; D003837:Deoxy Sugars; D016566:Organoselenium Compounds; D013402:Sugar Alcohols; D014753:Vinyl Compounds; D001089:Arabinose