DBU assisted expeditious synthesis of glycosyl dienes via glycosylated beta-hydroxy esters |
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Authors: | Verma Shyam S Dwivedi Namrata Singh Biswajit K Tripathi Rama P |
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Affiliation: | Medicinal and Process Chemistry Division, Central Drug Research Institute, Lucknow, India. |
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Abstract: | DBU catalyzed condensation of 3-O-benzyl(methyl)-5,6-dideoxy-1,2-O-isopropylidene-beta-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-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. |
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Keywords: | DBU Aldol type condensation Glycosyl uronates Glycosyl dienes |
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