DBU assisted expeditious synthesis of glycosyl dienes via glycosylated beta-hydroxy esters.
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.
Verma
Shyam S
SS
Medicinal and Process Chemistry Division, Central Drug Research Institute, Lucknow, India.
Dwivedi
Namrata
N
Singh
Biswajit K
BK
Tripathi
Rama P
RP
D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D000577:Amides / Q000737:chemistry; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry*; D002219:Carbamates / Q000737:chemistry; D004952:Esters / Q000737:chemistry*; D006031:Glycosylation; D008956:Models, Chemical; D014574:Uronic Acids / Q000737:chemistry
D000475:Alkenes; D000577:Amides; D019086:Bridged Bicyclo Compounds, Heterocyclic; D002219:Carbamates; D004952:Esters; D014574:Uronic Acids; C031033:1,8-diazabicyclo(5.4.0)undec-7-ene