A Novel, Readily Accessible Lactosaminyl Donor : N-Trichloroethoxycarbonyl-hexa-0-benzoyl-β-D-lactosaminyl Fluoride :

この論文にアクセスする

この論文をさがす

著者

抄録

A simple, preparatively satisfactory 10-step sequence is described for converting lactose into a novel, suitably blocked lactosaminyl donor: <i>N</i>-Trichloroethoxycarbonyl-<i>β</i>-<FONT SIZE="-2">D</FONT>-lactosaminyl fluoride (<b>5</b>). The key intermediate in this conversion is the particularly well-accessible oxime of lactosulosyl bromide (52% for the 6 steps from lactose), which on <i>α</i>-glycosidation with <i>p</i>-methoxybenzyl alcohol, oxime reduction, <i>N</i>-protection by Troc chloride, and the anomeric fluorination yields <b>5</b> (37% for the 4 steps). The utility of <b>5</b> as an effective donor was proved by the <i>β</i>-selective glycosylation of the primary 6-OH of 1,2 : 3,4-di-<i>O</i>-isopropylidene-<i>α</i>-<FONT SIZE="-2">D</FONT>-galactopyranose (<b>14</b>) and the 3-OH of methyl 2,4,6-tri-<i>O</i>-benzyl-<i>β</i>-<FONT SIZE="-2">D</FONT>-galactopyranoside (<b>16</b>), both affording the respective trisaccharides <b>15</b> and <b>18</b> in high yields. The latter, when subjected to <i>N</i>-deprotection, <i>N</i>-acetylation, and de-<i>O</i>-acylation gave, in 42% yield based on donor <b>5</b>, <i>β</i>-<FONT SIZE="-2">D</FONT>-Gal-(1→4)-<i>β</i>-<FONT SIZE="-2">D</FONT>-GlcNAc-(1→3)-<i>β</i>-<FONT SIZE="-2">D</FONT>-Gal-(1→Me, a core trisaccharide unit of immunologically important carbohydrate antigens.

収録刊行物

  • Bulletin of the Chemical Society of Japan

    Bulletin of the Chemical Society of Japan 68(4), 1172-1179, 1995-04-15

    The Chemical Society of Japan

参考文献:  46件中 1-46件 を表示

  • <no title>

    GOTTSCHALK A. ed

    Glycoproteins, 1972

    被引用文献1件

  • <no title>

    MONTRUEIL J.

    Adv. Carbohydr. Chem. Biochem. 37, 157, 1980

    被引用文献1件

  • <no title>

    ALLEN H. J.

    Glycoconjugates, 1992

    被引用文献2件

  • <no title>

    HAKOMORI S.

    J. Biol. Chem. 259, 4672, 1984

    被引用文献1件

  • <no title>

    SPRINGER T. A.

    Nature 346, 425, 1990

    被引用文献3件

  • <no title>

    SPRINGER T. A.

    Nature 349, 196, 1991

    被引用文献3件

  • <no title>

    KRUSE J.

    Nature 311, 153, 1984

    被引用文献1件

  • <no title>

    ARIGA T.

    J. Biol. Chem. 262, 848, 1987

    被引用文献1件

  • <no title>

    NAKANO T.

    Carbohydr. Res. 243, 43, 1993

    被引用文献2件

  • <no title>

    NILSSON M.

    J. Carbohydr. Chem. 9, 1, 1990

    被引用文献1件

  • <no title>

    PONPIPOM M. M.

    Tetrahedron Lett. 1978, 1717

    被引用文献2件

  • <no title>

    LEMIEUX R. U.

    Can. J. Chem. 60, 63, 1982

    被引用文献2件

  • <no title>

    ARNARP J.

    J. Chem. Soc., Perkin Trans. 1. 1982, 1841

    被引用文献1件

  • <no title>

    ARNARP J.

    J. Chem. Soc., Perkin Trans. 1. 1985, 535

    被引用文献1件

  • <no title>

    OGAWA T.

    Carbohydr. Res. 97, 81, 1981

    被引用文献2件

  • <no title>

    SCHMIDT R. R.

    Liebigs Ann. Chem. 1984, 1826

    被引用文献1件

  • <no title>

    GRUNDLER G.

    Carbohydr. Res. 135, 203, 1985

    被引用文献1件

  • <no title>

    JAIN R. K.

    Carbohydr. Res. 243, 385, 1993

    被引用文献1件

  • <no title>

    WINDHOLZ T. M.

    Tetrahedron Lett. 1967, 2555

    被引用文献1件

  • <no title>

    IMOTO M.

    Bull. Chem. Soc. Jpn. 60, 2205, 1987

    被引用文献11件

  • <no title>

    RANDALL J. L.

    Am. Chem. Soc. Symp. Ser. 374, 13, 1988

    被引用文献1件

  • <no title>

    SUZUKI K.

    Yuki Gosei Kagaku Kyukai Shi 51, 7181993

    被引用文献1件

  • <no title>

    SUZUKI K.

    Pure & Appl. Chem. 66, 1557, 1994

    被引用文献2件

  • <no title>

    JAIN R. K.

    J. Carbohydr. Chem. 7, 377, 1988

    被引用文献1件

  • <no title>

    WHITEFIELD D. M.

    Can. J. Chem. 68, 942, 1990

    被引用文献1件

  • <no title>

    LICHTENTHALER F. W.

    J. Org. Chem. 50, 3505, 1985

    被引用文献9件

  • <no title>

    OIKAWA Y.

    Tetrahedron Lett. 23, 885, 1982

    被引用文献12件

  • <no title>

    JOHANSSON R.

    J. Chem. Soc., Perkin Trans. 1 1984, 2371

    被引用文献5件

  • <no title>

    LICHTENTHALER F. W.

    Liebigs Ann. Chem. 1985, 1659

    被引用文献7件

  • <no title>

    HERSCOVICI J.

    J. Chem. Soc., Perkin Trans 1 1988, 1219

    被引用文献2件

  • <no title>

    KARPIESIUK W.

    J. Carbohydr. Chem. 9, 909, 1990

    被引用文献1件

  • <no title>

    GIANNIS A.

    Angew. Chem., Int. Ed. Engl. 28, 218, 1989

    被引用文献2件

  • <no title>

    SCHMIDT R. R.

    Angew. Chem., Int. Ed. Engl. 25, 212, 1986

    被引用文献23件

  • <no title>

    SCHMIDT R. R.

    Pure Appl. Chem. 61, 1257, 1989

    被引用文献2件

  • <no title>

    OHLE H.

    Ber. 58, 2585, 1925

    被引用文献2件

  • <no title>

    MUKAIYAMA T.

    Chem. Lett. 1981

    被引用文献1件

  • <no title>

    MUKAIYAMA T.

    Chem. Lett. 1983, 935

    被引用文献7件

  • <no title>

    KOHATA K.

    Carbohydr. Res. 132, 127, 1984

    被引用文献1件

  • <no title>

    SUZUKI K.

    Tetrahedron Lett. 30, 4853, 1989

    被引用文献8件

  • <no title>

    SUZUKI K.

    Tetrahedron Lett. 30, 6879, 1989

    被引用文献5件

  • <no title>

    KAJI E.

    Bull. Chem. Soc. Jpn. 61, 1291, 1988

    被引用文献6件

  • <no title>

    KAJI E.

    Trends Glycosci. Glycotechnol. 5, 121, 1993

    被引用文献6件

  • <no title>

    KAJI E.

    Bull. Chem. Soc. Jpn. 67, 1130, 1994

    被引用文献2件

  • <no title>

    HOUNSELL E. F.

    Chem. Soc. Rev. 16, 161, 1987

    DOI 被引用文献1件

  • <no title>

    MARANDUBA A.

    Carbohydr. Res. 151, 105, 1986

    DOI 被引用文献1件

  • <no title>

    ARNARP J.

    J. Chem. Soc., Perkin Trans. 1 1981, 2070

    DOI 被引用文献2件

各種コード

  • NII論文ID(NAID)
    10008888888
  • 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