Synthesis of erythro and threo furanoid glycals from 1- and 2-phenylselenenyl-carbohydrate derivatives.
Differently protected erythro and threo furanoid glycals were synthesized by selenoxide elimination when phenyl 1-selenoglycosides were treated in oxidizing conditions (tBuOOH, Ti(O(i)Pr)(4), Et(2)(i)PrN). The phenyl 1-selenoglycosides were obtained from methyl 2-deoxy-D-erythro-pentofuranoside by protection of the primary hydroxyl or both hydroxyls and further reaction with PhSeH in the presence of BF(3).Et(2)O. Erythro and threo furanoid glycals were also prepared by treating 2-deoxy-2-phenylselenenyl-1,4-anhydrocyclitols under similar conditions. The 2-deoxy-2-phenylselenenyl-1,4-anhydrocyclitols were obtained from 4-pentene-1,2,3-triols by a 5-endo selenium electrophilic induced cyclization.
Bravo
F
F
Departament de Química Analítica i Química Orgànica, Universitat Rovira i Virgili, Pça. Imperial Tarraco 1, E-43005, Tarragona, Spain.
Kassou
M
M
Díaz
Y
Y
Castillón
S
S
D002241:Carbohydrates / Q000737:chemistry*; D004896:Erythritol / Q000031:analogs & derivatives / Q000737:chemistry*; D005663:Furans / Q000737:chemistry; D006027:Glycosides / Q000138:chemical synthesis*; D010084:Oxidation-Reduction; D012643:Selenium / Q000737:chemistry*; D013402:Sugar Alcohols / Q000737:chemistry*
D002241:Carbohydrates; D005663:Furans; D006027:Glycosides; D013402:Sugar Alcohols; C003460:threitol; D012643:Selenium; D004896:Erythritol