Heptanosides from galactose-derived oxepenes via stereoselective addition reactions.
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.
Batchelor
Rhys
R
Centre for Biodiscovery, Victoria University of Wellington, Wellington, New Zealand.
Harvey
Joanne E
JE
Northcote
Peter T
PT
Teesdale-Spittle
Paul
P
Hoberg
John O
JO
D005690:Galactose / Q000737:chemistry*; D006539:Heptoses / Q000737:chemistry*; D015394:Molecular Structure; D010082:Oxepins / Q000737:chemistry*; D013237:Stereoisomerism
D006539:Heptoses; D010082:Oxepins; D005690:Galactose