Versatile Synthon for Chirally β-Deuterated L-Amino Acids and Synthesis of (3R)- and (3S)-[3-^2H_1]-L-Serine
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概要
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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-^2H_1]-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)-[3-2H_1]-L-serine. Further transformation of the crucial halomethyl group of 4a-c was also pursued to extend this methodology.
- 社団法人日本農芸化学会の論文
- 1996-08-23
著者
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EGUCHI Tadashi
Department of Chemistry and Materials Science, Tokyo Institute of Technology
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KAKINUMA Katsumi
Department of Chemistry, Tokyo Institute of Technology
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Eguchi T
Tokyo Inst. Technol. Tokyo Jpn
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Eguchi Tadashi
Department Of Chemistry And Materials Science Tokyo Institute Of Technology
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MAEDA Yutaka
Department of Chemistry, Tokyo Gakugei University
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Kakinuma Katsumi
Department Of Chemistry And Materials Science Tokyo Institute Of Technology
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Tago Keiko
Department Of Chemistry Tokyo Institute Of Technology
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Maeda Yutaka
Department Of Applied Biological Science Tokyo University Of Science
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Eguchi Tadashi
Department Of Chemistry & Materials Science Tokyo Institute Of Technology
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Maeda Yutaka
Department Of Chemistry Tokyo Institute Of Technology
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