Synthesis 1990; 1990(6): 533-534
DOI: 10.1055/s-1990-26932
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Acidic Opening of the Dihydropyran Ring of Hexa-O-acetyl-D-lactal and Subsequent Chain Elongation. Novel Approach to the Synthesis of Low Molecular Weight O-Glycosides Containing a Diacetoxypolyene Aglycone Moiety

G. A. Tolstikov* , A. G. Tolstikov, O. F. Prokopenko, L. M. Khalilov, V. N. Odinokov
  • *Institute of Chemistry, USSR Acad. Sci. Ural Department, Bashkirian Research Centre, Ufa, USSR
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17. September 2002 (online)

Low molecular weight O-glycosides containing a diacetoxypolyene aglycone moiety were prepared by chain elongation with phosphoranes or with a phosphonate of (2E,4S,5R)-5,6-diacetoxy-4-(2,3,4,6-tetra-O-acetyl-ß-D-galactopyranyloxy) -2-hexenal (2), which was prepared from hexa-O-acetyl-D-lactal by acidic ring opening and subsequent acetylation.