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

摘要

DBU catalyzed condensation of 3-O-benzyl(methyl)-5,6-dideoxy-1,2-O-isopropylidene-beta-L-threo-hept-4-enofuranuron-ates with different aldehydes produces the corresponding 3-O-benzyl(methyl)-6-carbethoxy-5,6-dideoxy-1,2-O-isopropylidene-7-phen-yl-beta-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-beta-L-threo-hept-4,6-dienofuranose in moderate to good yields.