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We recently reported that ( E )-5'-vinylphosphonate (5'-VP) is a metabolically-stable phosphate mimic for siRNA and demonstrated that 5'-VP improves the potency of the fully modified siRNAs in vivo. Here, we report an alternative synthesis of 5'-VP modified guide strand using S -pivaloyl-2-thioethyl ( t Bu-SATE) protecting group. The t Bu-SATE group is readily removed during the final cleavage of the oligonucleotide from the solid support and providing a more convenient route for the synthesis of siRNA guide strand carrying a 5'-vinylphosphonate.

S-Acyl-2-Thioethyl: A Convenient Base-Labile Protecting Group for the Synthesis of siRNAs Containing 5′-Vinylphosphonate