201297-40-7Relevant academic research and scientific papers
Synthesis and characterization of β-O-Tosyldehydroserine as a precursor of dehydroamino acids
Nakazawa, Takashi,Suzuki, Tomiko,Ishii, Masako
, p. 8951 - 8954 (1997)
β-O-Tosyldehydroserine 3 is prepared directly by the oxidation of the corresponding serine derivative 1 with dimethyl sulfoxide which is activated by p-toluenesulfonyl chloride. The enol tosylate 3 retains reactivities characteristic of aldehydes like those expected for the corresponding dehydroserine derivative 2. A typical reaction of 3 includes substitution of the tosyl group with nucleophiles such as primary and secondary amines, leading to other dehydroamino acids.
Synthesis of α,β-dehydrotryptophan by reaction of indole with the β-(N-methylamino)dehydroalanine derivative
Nakazawa, Takashi,Ishii, Masako,Musiol, Hans-Juergen,Moroder, Luis
, p. 1381 - 1384 (2007/10/03)
α,β-Dehydrotryptophan 4 is synthesized by a sequence of reactions starting with the corresponding serine derivative 1. This procedure includes substitution reaction between indole and the methylamino group of the β-(N-methylamino)dehydroalanine derivative 3 in acetic acid. The key intermediate 3 is obtained by oxidation of 1 with dimethylsulfoxide activated by p-toluenesulfonyl chloride, followed by reaction of the resulting β-O-tosyldehydroserine 2 with methylamine.
