6533b85cfe1ef96bd12bd255

RESEARCH PRODUCT

Fluoreszierende silane als OH-selektive schutzgruppen

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description

Abstract Fluorescent tertiary silanes are synthesized which, under cesium fluoride/ imidazole activation, discriminate between primary and secondary OH groups. Serine n-butylamide reacts with [5-dimethylamino(1-naphthyl)]dimethylsilane ( 1 ) and diisopropyl[5-dimethylamino(1-naphthyl)]silane ( 2 ) to form the silyl ethers (−)- l -3-[5-dimethylamino(1-naphthyl)]-dimethylsilyloxy]serine n-butylamid ( 14 ) and (−)- l -3-[diisopropyl[5-dimethylamino(1-naphthyl)]silyloxy]serine n-butylamid ( 15 ) exclusively. The silyl ethers are cleaved on treatment with H 2 F 2 , forming the corresponding fluorescent silyl fluorides. Absorption and fluorescence data as well as stability data for the hydrolysis and cleavage by fluoride ions are reported for some silyl ethers.