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Synthesis and characterization of β-O-tosyldehydroserine as a precursor of dehydroamino acids

✍ Scribed by Takashi Nakazawa; Tomiko Suzuki; Masako Ishii

Book ID: 104258374
Publisher: Elsevier Science
Year: 1997
Tongue: French
Weight: 235 KB
Volume: 38
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(97)10360-4

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✦ Synopsis

fl-O-Toryldehydroserine 3 is prepared directly by the oxidation of the corresponding serine derivative 1 with dimethyl snlfoxide which is activated by p-toinenesulfonyl 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.

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