Preparation of 2-Hydroxymethylated Aldose by the Stereospecific Rearrangement of Ketose

DOI PDF 1 Citations 22 References
  • Ryoji Yanagihara
    Department of Applied Chemistry, Faculty of Science and Technology, Keio University3-14-1 Hiyoshi Kohhoku-ku, Yokohamashi 223
  • Jun Egashira
    Department of Applied Chemistry, Faculty of Science and Technology, Keio University3-14-1 Hiyoshi Kohhoku-ku, Yokohamashi 223
  • Sadao Yoshikawa
    Department of Applied Chemistry, Faculty of Science and Technology, Keio University3-14-1 Hiyoshi Kohhoku-ku, Yokohamashi 223
  • Shuichi Osanai
    Department of Applied Chemistry, Faculty of Science and Technology, Keio University3-14-1 Hiyoshi Kohhoku-ku, Yokohamashi 223

Search this article

Abstract

<jats:title>Abstract</jats:title> <jats:p>A simple one-stage reaction system which yields 2-C hydroxymethylated aldopentose has been investigated. Four different 2-C branched aldopentoses (2-C hydroxymethylated d-arabinose, d-ribose (Hamamelose), l-lyxose, and d-xylose) were prepared from the corresponding ketoses (d-psicose, d-fructose, l-sorbose, and d-tagatose, respectively). These branched sugars were synthesized by a similar mechanism to the 2-C epimerization of aldose using a nickel complex. It was confirmed that the isomerization of ketose to the side-branched sugar proceeded in the ternary nickel complex through a sequence of stereospecific rearrangements in the sugar. The yields were dependent upon the structure of the substrate ketose and the nickel-ethylenediamine complex. N,N′-Dialkylated cyclohexanediamines were the most suitable ligands for preparing the 2-C hydroxymethylated branched chain sugar.</jats:p>

Journal

Citations (1)*help

See more

References(22)*help

See more

Keywords

Details 詳細情報について

Report a problem

Back to top