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Heptanosides from Galactose-Derived Oxepenes via Stereoselective Addition Reactions

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journal contribution
posted on 16.10.2009, 00:00 by Rhys Batchelor, Joanne E. Harvey, Peter T. Northcote, Paul Teesdale-Spittle, John O. Hoberg
Addition reactions to a 3,4-anhydroheptanose gave heptanoside analogues of carbohydrate derivatives in good to excellent stereochemical purity. Characterization of the products by 1H and 13C 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.