Elsevier

Tetrahedron

Volume 53, Issue 34, 25 August 1997, Pages 11753-11766
Tetrahedron

Iodine: A versatile reagent in carbohydrate chemistry IV. Per-O-acetylation, regioselective acylation and acetolysis

https://doi.org/10.1016/S0040-4020(97)00742-4Get rights and content

Abstract

Iodine has been found to be an effective Lewis acid for promoting the per-O-acetylation of unprotected sugars. Under controlled conditions it can bring about regioselective acylation of carbohydrate derivatives. At higher concentration and with longer reaction times, iodine can effect the selective acetolysis of benzyl ether-protected primary hydroxyl groups. All of these reactions proceed in high yield, are easy to carry out and make use of readily available iodine, which is both cheap and easy to handle.

Iodine has been found to be an excellent reagent for converting free sugars into their per-O-acetylated derivatives. Under controlled conditions selective partial acylation or acetolysis can be achieved.

  1. Download : Download full-size image

References (25)

  • F. Dasgupta et al.

    Carbohydr. Res.

    (1980)
  • R. Kuhn et al.

    Chem. Ber.

    (1966)
  • K.P.R. Kartha et al.

    J. Carbohyr. Chem.

    (1986)
  • K. Jansson et al.

    J. Org. Chem.

    (1988)
  • A. Hasegawa et al.

    Carbohydr. Res.

    (1992)
  • J.K. Dale et al.

    J. Am. Chem. Soc.

    (1930)
  • D. Barbry et al.

    Synth. Commun.

    (1995)
    R. Yanada et al.

    Synlett.

    (1995)
    K. Orito et al.

    Synthesis

    (1995)
    R. Madsen et al.

    J. Org. Chem.

    (1995)
    A.R. Vaino et al.

    J. Chem. Soc., Chem. Commun.

    (1996)
    A.R. Vaino et al.

    Synlett.

    (1995)
    J.M. Lin et al.

    Tetrahedron Lett.

    (1996)
    O. Kitagawa et al.

    Tetrahedron Lett.

    (1995)
    A.D. Jones et al.

    J. Chem. Soc., Chem. Commun.

    (1996)
    T. Langer et al.

    Tetrahedron Lett.

    (1995)
    K.M. Kim et al.

    Tetrahedron Lett.

    (1996)
  • K.P.R. Kartha et al.

    Tetrahedron Lett.

    (1996)
  • K.P.R. Kartha

    Tetrahedron Lett.

    (1986)
    W.A. Szarek et al.

    Tetrahedron Lett.

    (1986)
  • C.G.J. Verhart et al.

    Recl. Trav. Chim. Pays-Bas

    (1996)
  • Cited by (0)

    Presented in part at the XVIIIth International Carbohydrate Symposium, Milan, Italy, 1996. For part III see Kartha, K.P.R.; Aloui, M.; Field, R.A. Tetrahedron Lett., 1996, 37, 8807.

    View full text