title: Heptanosides from galactose-derived oxepenes via stereoselective addition reactions.
abstract: Addition reactions to a 3,4-anhydroheptanose gave heptanoside analogues of carbohydrate derivatives in good to excellent stereochemical purity. Characterization of the products by (1)H and (13)C NMR, COSY, HSQC-DEPT, HMBC, 1D TOCSY, and NOE experiments were performed to obtain the stereochemistry of addition. The 3,4-anhydroheptanose used in this study is obtained from the ring-expansion of a cyclopropanated galactal and thus demonstrates the synthetic utility of heptanose synthesis via cyclopropanated carbohydrates.
authors.affiliation: Centre for Biodiscovery, Victoria University of Wellington, Wellington, New Zealand.
authors.forename: Rhys
authors.initials: R
authors.lastname: Batchelor
authors.forename: Joanne E
authors.initials: JE
authors.lastname: Harvey
authors.forename: Peter T
authors.initials: PT
authors.lastname: Northcote
authors.forename: Paul
authors.initials: P
authors.lastname: Teesdale-Spittle
authors.forename: John O
authors.initials: JO
authors.lastname: Hoberg
mesh_terms: D005690:Galactose / Q000737:chemistry*; D006539:Heptoses / Q000737:chemistry*; D015394:Molecular Structure; D010082:Oxepins / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D006539:Heptoses; D010082:Oxepins; D005690:Galactose