Versatile synthon for chirally β-deuterated L-amino acids and synthesis of (3R)- and (3S)-[3-2H1]-L-serine

Article abstract of DOI:10.1271/bbb.60.1248

A divergent and highly enantioselective synthetic methodology for producing chirally β-deuterated L-amino acids was developed. This method is based upon the chirality transcription approach, using diacetone-D-glucos-3- ulose (1) as a template. 3-C-[2-²H₁]-Ethenyl-3-O-(N- benzyl)methylthioformimidoyl-D-allo-derivatives (3b and 3c), which are easily accessible from 1, were subjected to halonium ion-assisted cyclization to afford highly diastereoselectively and efficiently versatile 5-membered cyclic carbamate synthons having a stereochemically defined deuterated halomethyl group (4c and 4d, respectively). Subsequent straightforward transformation of these synthons gave rise to (3R)- and (3S)-[3-²H₁]-L- serine. Further transformation of the crucial halomethyl group of 4a-c was also pursued to extend this methodology.

Full text of DOI:10.1271/bbb.60.1248

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Versatile Synthon for Chirally β-Deuterated L-Amino
Acids and Synthesis of (3R)- and (3S)-[3–2H1-l-Serine*
Yutaka Maedaa, Keiko Tagoa, Tadashi Eguchia & Katsumi Kakinumaa
a Department of Chemistry, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo
152, Japan
Published online: 12 Jun 2014.
To cite this article: Yutaka Maeda, Keiko Tago, Tadashi Eguchi & Katsumi Kakinuma (1996) Versatile Synthon for Chirally
β-Deuterated L-Amino Acids and Synthesis of (3R)- and (3S)-[3–2H1-l-Serine*, Bioscience, Biotechnology, and Biochemistry,
60:8, 1248-1254, DOI: 10.1271/bbb.60.1248
To link to this article: http://dx.doi.org/10.1271/bbb.60.1248
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