Synthesis of mono- and dideoxygenated α,α-trehalose analogs

In this work, we describe the synthesis and NMR characterization of four mono- and four dideoxygenated analogs of alpha,alpha-D-trehalose, The symmetrical (2,2'-, 3,3'-, 4,4'- and 6,6'-) dideoxy analogs were obtained via selective protection and subsequent radical deoxygenation ofthe desired hydroxyl group set. The unsymmetrical (2'-, 3'-, 4- and 6'-) monodeoxy analogs were synthesized by desymmetrization of alpha,alpha-trehalose and subsequent deoxygenation under radical conditions. Complete assignment of all 1H and C-13 resonances in the spectra of these deoxytrehaloses was achieved through the extensive use of 2D {H-1,H-1} and {(HC)-H-1-C-13} correlation NMR experiments. The synthesis of these trehalose analogs sets the stage for future biochemical and NMR-based studies to probe the substrate interactions of trehalose with the recently identified mycobacterial sulfotransferase StfO. (c) 2007 Elsevier Ltd. All rights reserved.