Attempted synthesis of 2-acetamido and 2-amino derivatives of salacinol. Ring opening reactions.
The attempted synthesis of the 2-acetamido and 2-amino derivatives of salacinol, a naturally occurring glycosidase inhibitor, is described. Reaction of the protected acetamidothioarabinitol unit with the cyclic sulfate derived from L-erythritol gave the corresponding sulfonium sulfate, which underwent ring opening to give an acyclic amido sulfate. The corresponding reaction of the protected azidothioarabinitol unit with the cyclic sulfate proceeded to give the sulfonium sulfate. However, upon reduction of the azido function to an amine it formed an acyclic ammonium sulfate.
Choubdar
Niloufar
N
Department of Chemistry, Simon Fraser University, Burnaby, BC, Canada V5A 1S6.
Pinto
B Mario
BM
D000588:Amines; D000645:Ammonium Sulfate; D001386:Azides; D004791:Enzyme Inhibitors / Q000138:chemical synthesis; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors; D006865:Hydrogenation; D013402:Sugar Alcohols / Q000138:chemical synthesis*; D013431:Sulfates / Q000138:chemical synthesis* / Q000737:chemistry
D000588:Amines; D001386:Azides; D004791:Enzyme Inhibitors; D013402:Sugar Alcohols; D013431:Sulfates; C427963:salacinol; D006026:Glycoside Hydrolases; D000645:Ammonium Sulfate