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

Shigeru Nishiyama Department of Chemistry, Faculty of Science and Technology, Keio University Hiyoshi, Yokohama, 223, Japan

Tadaaki Ohgiya Department of Chemistry, Faculty of Science and Technology, Keio University Hiyoshi, Yokohama, 223, Japan

Shosuke Yamamura Department of Chemistry, Faculty of Science and Technology, Keio University Hiyoshi, Yokohama, 223, Japan

Kuniki Kato Research Laboratories, Pharmaceuticals Group, Nippon Kayaku Co. Ltd., 3-31-12 Shimo, Kita-ku, Tokyo, 115, Japan

Tomohisa Takita Research Laboratories, Pharmaceuticals Group, Nippon Kayaku Co. Ltd., 3-31-12 Shimo, Kita-ku, Tokyo, 115, Japan

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.

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

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

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