Oxetanocin—Oxetanose Chemistry: Lewis Acid Promoted Glycosidations of the D-Erythrooxetanose Derivatives

Abstract Upon treatment of 1-O-acetyl-D-erythrooxetanoses (17a,b and 26) with trimethylsilyl N-benzoyladenine or allyltrimethylsilane in the presence of SnCl4, the ring expanded products (18, 19 and 29) or the acyclic compounds (27 and 28) were obtained. The reaction mechanism involving a novel ring opening process is discussed.