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
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.