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

Title
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
Authors
최환근박동식이원구심태보
Keywords
D-AB1/L-AB1; D-DIX/L-DIX; Natural product; Efficient synthesis; Chiral aziridines
Issue Date
2013-10
Publisher
Tetrahedron letters
Citation
VOL 54, NO 43, 5775-5777
Abstract
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.
URI
http://pubs.kist.re.kr/handle/201004/45851
ISSN
00404039
Appears in Collections:
KIST Publication > Article
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