title: Design, synthesis, and biological activities of some branched carbasugars: construction of a substituted 6-oxabicyclo[3.2.1]nonane skeleton.
abstract: Transformation of cyclohexa-2,4-diene-1,2-diylbis(methylene) diacetate to various carbasugars is described. Photooxygenation of a cyclohexadiene derivative gave a bicyclicendoperoxide, which was reduced with thiourea to [2-[(acetyloxy)methyl]cyclohexa-2,4-dien-1-yl]methyl acetate. Epoxidation of the remaining double bond followed by epoxide ring-opening and hydrolysis of the acetate groups gave one of the target hexols. The bicyclic endoperoxide was rearranged to a diepoxide with CoTPP. The diepoxide was reacted with sulfamic acid in acetic anhydride, resulting in the formation of a new branched carbasugar as well as in the formation of cyclitols with a 6-oxabicyclo[3.2.1]nonane skeleton. The mechanism of the formation of the products is discussed. The inhibition activity of six cyclitol derivatives was tested against α-glycosidase.
authors.affiliation: Department of Chemistry, Sakarya University, 54100 Sakarya, Turkey. baranarif@yahoo.com
authors.forename: Arif
authors.initials: A
authors.lastname: Baran
authors.forename: Sinem
authors.initials: S
authors.lastname: Çambul
authors.forename: Mehmet
authors.initials: M
authors.lastname: Nebioglu
authors.forename: Metin
authors.initials: M
authors.lastname: Balci
mesh_terms: D000473:Alkanes / Q000138:chemical synthesis* / Q000737:chemistry; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D060326:Chemistry Techniques, Synthetic / Q000379:methods; D054812:Cyclitols / Q000138:chemical synthesis* / Q000737:chemistry; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors / Q000737:chemistry*; D015394:Molecular Structure
chemical_list: D000473:Alkanes; D001643:Bridged Bicyclo Compounds; D054812:Cyclitols; D006026:Glycoside Hydrolases; C017573:nonane