DBU assisted expeditious synthesis of glycosyl dienes via glycosylated β-hydroxy esters

DBU catalyzed condensation of 3-O-benzyl(methyl)-5,6-dideoxy-1,2-O-isopropylidene-β-l-threo-hept-4-enofuranuronates with different aldehydes produces the corresponding 3-O-benzyl(methyl)-6-carbethoxy-5,6-dideoxy-1,2-O-isopropylidene-7-phenyl-β-l-threo-hept-4-enofuranoses. The latter on treatment with methanesulfonyl chloride followed by DBU catalyzed E2 reaction of the methanesulfonyloxy intermediates gave the respective 3-O-benzyl(methyl)-6-carbethoxy-5,6,7-trideoxy-1,2-O-isopropylidene-7-phenyl-β-l-threo-hept-4,6-dienofuranose in moderate to good yields.

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