Synthesis of pseudo saccharide precursors through 'off template site' Michael-Wittig reaction on sugar derived enal

Abstract

[3+3] 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. ©ARKAT.