Methoxydioxasilepane: A Versatile and Stable Synthetic Precursor of Trimethoxysilane

Abstract

This study introduces aryl(methoxy)dioxasilepane as a versatile and stable precursor for aryl(trimethoxy)silanes. We conducted a quantitative assessment of the stability of this silicon moiety under acidic and basic conditions, demonstrating its superior stability compared to triethoxysilane, and methyl- or (trifluoroethoxy)dioxasilepanes. The synthetic utility of the methoxydioxasilepane unit was further elucidated through an examination of its orthogonality and selective functionalization capabilities. Notably, we developed an efficient method for the conversion of methoxydioxasilepane into trimethoxysilane. This method underscores the potential of a methoxydioxasilepane as a surrogate in multistep syntheses of silanetriols, which offer advantages in the development of silicon-based bioisosteres for medicinal chemistry applications.

Key words

silanols - silanetriols - alkoxysilanes - bioisosteres - dioxasilepanes

Publikationsverlauf

Eingereicht: 04. Juli 2024

Angenommen nach Revision: 02. September 2024

Accepted Manuscript online:
02. September 2024

Artikel online veröffentlicht:
26. September 2024

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