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Annulation protocol at an'off template site' on the sugar derived enal synthon effectively resulted in the formation of C-C linked pseudo saccharide precursors. Thus, the enolate of phosphorane generated from ethyl acetoacetate first undergoes a Michael reaction on the enal followed by a Wittig reaction to furnish the target saccharides, where the chirality is very effectively translated from the parent sugar.

Synthesis of pseudo saccharide precursors through ‘off template site’ Michael –Wittig reaction on sugar derived enal