Elsevier

Carbohydrate Research

Volume 40, Issue 2, April 1975, Pages 285-298
Carbohydrate Research

Derivatives of β-D-fructofuranosyl α-D-galactopyranoside

https://doi.org/10.1016/S0008-6215(00)82610-5Get rights and content

Abstract

De-etherification of 6,6′-di-O-tritylsucrose hexa-acetate (2) with boiling, aqueous acetic acid caused 4→6 acetyl migration and gave a syrupy hexa-acetate 14, characterised as the 4,6′-dimethanesulphonate 15. Reaction of 2,3,3′4′,6-penta-O-acetylsucrose (5) with trityl chloride in pyridine gave a mixture containing the 1′,6′-diether 6 the 6′-ether 9, confirming the lower reactivity of HO-1′ to tritylation. Subsequent mesylation, detritylation, acetylation afforded the corresponding 4-methanesulphonate 8 1′,4-dimethanesulphonate 11. Reaction of these sulphonates with benzoate, azide, bromide, and chloride anions afforded derivatives of β-D-fructofuranosyl α-D-galactopyranoside (29) by inversion of configuration at C-4. Treatment of the 4,6′-diol 14 the 1,′4,6′-triol 5, the 4-hydroxy 1′,6′-diether 6 with sulphuryl chloride effected replacement of the free hydroxyl groups and gave the corresponding, crystalline chlorodeoxy derivatives. The same 4-chloro-4-deoxy derivative was isolated when the 4-hydroxy-1′,6′-diether 6 was treated with mesyl chloride in N,N-dimethylformamide.

References (25)

  • R. Khan et al.

    Carbohyd. Res.

    (1975)
  • R. Khan

    Carbohyd. Res.

    (1972)
  • D.S. Feingold et al.

    J. Biol. Chem.

    (1957)
  • A.C. Richardson

    Carbohyd. Res.

    (1969)
  • J.G. Buchanan et al.

    Carbohyd. Res.

    (1972)
  • L. Hough et al.

    Carbohyd. Res.

    (1973)
  • R.G. Edwards et al.

    Tetrahedron Lett.

    (1973)
  • L. Hough et al.

    Carbohyd. Res.

    (1972)
  • G.G. McKeown et al.

    Can. J. Chem.

    (1957)
  • B. Helferich

    Ber.

    (1921)
  • B. Helferich et al.

    Ber.

    (1923)
  • B. Helferich et al.

    Ber.

    (1925)
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