An efficient synthesis of 1,4-dideoxy-1,4-imino-D- and L-arabinitol and 1,4-dideoxy-1,4-imino-D- and L-xylitol from chiral aziridines
- An efficient synthesis of 1,4-dideoxy-1,4-imino-D- and L-arabinitol and 1,4-dideoxy-1,4-imino-D- and L-xylitol from chiral aziridines
- 최환근; 박동식; 이원구; 심태보
- D-AB1/L-AB1; D-DIX/L-DIX; Natural product; Efficient synthesis; Chiral aziridines
- Issue Date
- Tetrahedron letters
- VOL 54, NO 43, 5775-5777
- A highly efficient method for the synthesis of 1,4-dideoxy-1,4-imino-D- and L-arabinitol (D-AB1, 1 and
L-AB1, 3) and 1,4-dideoxy-1,4-imino-D- and L-xylitol (D-DIX, 2 and L-DIX, 4) starting from commercially
available chiral aziridines was developed. The general strategy employs a sequence involving two-carbon
homologation, dihydroxylation, and regioselective aziridine ring opening/intramolecular five-membered
iminosugar ring formation. The facile use of recrystallization to generate pure diastereomers makes the
routes more amenable to large-scale synthesis.
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