An acid-stable tert-butyldiarylsilyl (TBDAS) linker for solid-phase organic synthesis.
[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.
Diblasi
Christine M
CM
Molecular Pharmacology and Chemistry Program, Memorial Sloan-Kettering Cancer Center, 1275 York Avenue, Box 422, New York, New York 10021, USA.
Macks
Daniel E
DE
Tan
Derek S
DS
D000143:Acids / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D003432:Cross-Linking Reagents / Q000737:chemistry*; D012821:Silanes / Q000138:chemical synthesis / Q000737:chemistry
D000143:Acids; D003432:Cross-Linking Reagents; D012821:Silanes