An acid-stable tert-butyidiaryisilyl (TBDAS) linker for solid-phase organic synthesis

Division of Molecular Pharmacology & Chemistry, Memorial Sloan-Kettering Cancer Center, New York, New York, United States
Organic Letters (Impact Factor: 6.32). 05/2005; 7(9):1777-80. DOI: 10.1021/ol050370y
Source: PubMed

ABSTRACT [reaction: see text] A new, robust tert-butyldiarylsilyl (TBDAS) linker has been developed for solid-phase organic synthesis. This linker is stable to both protic and Lewis acidic reaction conditions, overcoming a significant limitation of previously reported silyl linkers. Solid-phase acetal deprotection, olefination, asymmetric allylation, and silyl protecting group deblocking reactions have been demonstrated with TBDAS-linked substrates.

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