Synthesis of carbohydrate-based vinyl selenides via Wittig-type reactions.
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.
Boutureira
Omar
O
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.
Matheu
M Isabel
MI
Díaz
Yolanda
Y
Castillón
Sergio
S
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*
D002241:Carbohydrates; D003837:Deoxy Sugars; D016566:Organoselenium Compounds; D013402:Sugar Alcohols; D014753:Vinyl Compounds; D001089:Arabinose