biostudies-literatureSaito HSumitomo FoundationCore Research for Evolutional Science and TechnologyJapan Society for the Promotion of Science9546-9555https://www.ebi.ac.uk/biostudies/studies/S-EPMC8278973biostudies-literatureUnknown12(27)Organic synthesis is performed based on precise choices of functional groups and reactions employed. In a multistep synthesis, an ideal functional group should be compatible with various reaction conditions and unaltered until it is subjected to a selective conversion. The current study was set out to search for a silicon functionality that meets these criteria. Here we have established a new silicon-based synthetic methodology centred on a bulky 7-membered dialkoxysilyl group (2,4,4,7,7-pentamethyl-1,3,2-dioxasilepan-2-yl) that uniquely has both stability and on-demand reactivity. The exceptional stability of this functional group was corroborated by both experimental and computational studies which demonstrated that key factors for its stability were a 7-membered structure and steric hinChemical scienceThe dioxasilepanyl group as a versatile organometallic unit: studies on stability, reactivity, and utility.PMC8278973JP18J22838JS21H01934JPMJCR19R4JP19H00895Shimokawa JSaito HYorimitsu HfalseThe dioxasilepanyl group as a versatile organometallic unit: studies on stability, reactivity, and utility.Organic synthesis is performed based on precise choices of functional groups and reactions employed. In a multistep synthesis, an ideal functional group should be compatible with various reaction conditions and unaltered until it is subjected to a selective conversion. The current study was set out to search for a silicon functionality that meets these criteria. Here we have established a new silicon-based synthetic methodology centred on a bulky 7-membered dialkoxysilyl group (2,4,4,7,7-pentamethyl-1,3,2-dioxasilepan-2-yl) that uniquely has both stability and on-demand reactivity. The exceptional stability of this functional group was corroborated by both experimental and computational studies which demonstrated that key factors for its stability were a 7-membered structure and steric hin2021-01-01T00:00:00Z2021 Jul2026-05-08T03:39:23.777Z2022-02-11T02:57:38.92ZS-EPMC82789733434992910.1039/d1sc02083h