Studies of Aminosugars. XI. Configurational Studies of Aminosugar Glycosides and Aminocyclitols by a Copper Complex Method

Abstract

Abstract An extensive study has been made of the determination of the rotational shift of aminosugars in three kinds of cuprammonium solutions, i. e., in solutions of tetramminecopper(II) sulfate, ammoniacal cuprous chloride and Cupra B, with special consideration of the spacial relationships between adjacent amino and hydroxyl groups in six-membered chair molecules. This paper is an extension of the work of Reeves which provided a tool for the determination of the spacial relationships between adjacent two-hydroxyl groups. Some significant generalizations have been obtained. About ten derivatives of glucosamine have been prepared, and their structures, as indicated by their rotational shifts, have been discussed. The absolute configurations of d- and l-trance-2-aminocyclohexanol have been successfully determined.