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

この論文にアクセスする

この論文をさがす

著者

    • YANAGIHARA Ryoji
    • Department of Applied Chemistry, Faculty of Science and Technology, Keio Rniversity
    • EGASHIRA Jun
    • Department of Applied Chemistry, Faculty of Science and Technology, Keio Rniversity
    • YOSHIKAWA Sadao
    • Department of Applied Chemistry, Faculty of Science and Technology, Keio Rniversity
    • OSANAI Shuichi
    • Department of Applied Chemistry, Faculty of Science and Technology, Keio Rniversity

抄録

A simple one-stage reaction system which yields 2-C hydroxymethylated aldopentose has been investigated. Four different 2-C branched aldopentoses (2-C hydroxymethylated <FONT SIZE="-2">D</FONT>-arabinose, <FONT SIZE="-2">D</FONT>-ribose (Hamamelose), <FONT SIZE="-2">L</FONT>-lyxose, and <FONT SIZE="-2">D</FONT>-xylose) were prepared from the corresponding ketoses (<FONT SIZE="-2">D</FONT>-psicose, <FONT SIZE="-2">D</FONT>-fructose, <FONT SIZE="-2">L</FONT>-sorbose, and <FONT SIZE="-2">D</FONT>-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. <i>N</i>,<i>N</i>′-Dialkylated cyclohexanediamines were the most suitable ligands for preparing the 2-C hydroxymethylated branched chain sugar.

収録刊行物

  • Bulletin of the Chemical Society of Japan

    Bulletin of the Chemical Society of Japan 68(1), 237-242, 1995-01-15

    The Chemical Society of Japan

参考文献:  17件中 1-17件 を表示

  • <no title>

    TANASE T.

    Inorg. Chem 27, 4085, 1988

    被引用文献5件

  • <no title>

    FUKUSHIMAK K.

    Nipon Kagaku Kaishi 1988, 585

    被引用文献1件

  • <no title>

    INABA K.

    Carbohydr. Res. 109, 189, 1990

    被引用文献1件

  • <no title>

    YAMAUCHI T.

    Carbohydr. Res. 204, 233, 1990

    被引用文献4件

  • <no title>

    HATAYA K.

    J. Chem. Soc., Chem. Commun. 1991, 1246

    被引用文献3件

  • <no title>

    YANAGIHARA R.

    Bull. Chem. Soc. Jpn. 66, 2268, 1993

    被引用文献2件

  • <no title>

    OSANAI S.

    J. Chem. Soc., Perkin Trans. 1. 1993, 1937

    被引用文献2件

  • <no title>

    YANAGIHARA R.

    Chem. Lett. 1992, 89

    被引用文献3件

  • <no title>

    EL KHADEM H. S.

    Carbohydrate Chemistry, Monosaccharides and Their Oligomers 103, 1988

    被引用文献1件

  • <no title>

    EL KHADEM H. S.

    Carbohydr. Res 185, 51, 1989

    被引用文献1件

  • <no title>

    TAKIZAWA S.

    J. Am. Chem. Soc. 102, 7969, 1980

    被引用文献2件

  • <no title>

    MATSUMOTO T.

    Chem. Lett. 1984, 1819

    被引用文献1件

  • <no title>

    HO P. -T.

    Tetrahedron Lett. 1978, 1623

    被引用文献2件

  • <no title>

    SCHILLING G.

    Justus Liebigs Ann. Chem. 1977, 1475

    被引用文献2件

  • <no title>

    PIGMAN W.

    The Carbohydrates, Chemistry and Biochemistry IB Cha 22, 1980

    被引用文献1件

  • <no title>

    SWEELY C. C.

    J. Am. Chem. Soc. 85, 2947, 1963

    被引用文献1件

  • <no title>

    KING-MORRIS M. J.

    Carbohydr. Res 154, 29, 1986

    DOI 被引用文献1件

各種コード

  • NII論文ID(NAID)
    10008884888
  • NII書誌ID(NCID)
    AA00580132
  • 本文言語コード
    ENG
  • 資料種別
    ART
  • ISSN
    00092673
  • データ提供元
    CJP書誌  J-STAGE 
ページトップへ