As a part of a program to develop novel, versatile methods and strategies for S-thiodisaccharide synthesis, we have recently reported the synthesis and evaluation of differently functionalized S-1, 4-thiodisacharides and their sulfones. Here we describe further assessment of the stereoselective Michael addition of active 1-thiosugars to L-arabinose enones. In accordance with this new stereoselective concept, the synthesis of first novel 1, 5-thidisacharides is achieved. We demonstrated that activation of the conjugate Michael addition with various bases such as Et3N, and TMG allows the stereoselective synthesis of S-1-5 linked thiodisacahrides with no protecting group manipulation during and after functionalization.
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Back to The 37th Middle Atlantic Regional Meeting (May 22-25, 2005)