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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Heptanosides from galactose-derived oxepenes via stereoselective addition reactions
Rhys Batchelor1, Joanne E Harvey, Peter T Northcote
1Centre for Biodiscovery, Victoria University of Wellington, Wellington, New Zealand.
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.
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