tert-Buyldiphenylsilylethyl ("TBDPSE"): a practical protecting group for phenols.
[reaction: see text] A new protection group for phenols, the 2-(tert-butyldiphenylsilyl)ethyl (TBDPSE) group, has been prepared and investigated. Protection of a variety of substituted phenols proceeds in good to excellent yield. The group is stable to mild acid, base, hydrogenolysis conditions, and lithium/halogen exchange on the protected phenol. Removal is achieved with strong acid or standard fluoride treatment.
Gerstenberger
Brian S
BS
Department of Chemistry and Biochemistry, University of California, Santa Cruz, California 95064, USA.
Konopelski
Joseph P
JP
D000440:Butanols / Q000138:chemical synthesis / Q000737:chemistry*; D000431:Ethanol / Q000737:chemistry*; D015394:Molecular Structure; D010636:Phenols / Q000737:chemistry*; D014443:Tyrosine / Q000737:chemistry
D000440:Butanols; D010636:Phenols; D000431:Ethanol; D014443:Tyrosine