Choi, Hwan Geun Park, Dong-Sik Lee, Won Koo Sim, Taebo 2024-01-20T11:05:04Z 2024-01-20T11:05:04Z 2021-09-05 2013-10-23 0040-4039 https://pubs.kist.re.kr/handle/201004/127535 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. (c) 2013 Elsevier Ltd. All rights reserved. English PERGAMON-ELSEVIER SCIENCE LTD POLYHYDROXYLATED PYRROLIDINES GLYCOGEN-PHOSPHORYLASE CONCISE SYNTHESIS INHIBITORS IMINOSUGARS CLEAVAGE PERSPECTIVES CYCLIZATION AZASUGARS ACID 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 Article 10.1016/j.tetlet.2013.08.040 1 TETRAHEDRON LETTERS, v.54, no.43, pp.5775 - 5777 TETRAHEDRON LETTERS 54 43 5775 5777 scie scopus 000325122100003 2-s2.0-84884290031 Chemistry, Organic Chemistry Article POLYHYDROXYLATED PYRROLIDINES GLYCOGEN-PHOSPHORYLASE CONCISE SYNTHESIS INHIBITORS IMINOSUGARS CLEAVAGE PERSPECTIVES CYCLIZATION AZASUGARS ACID D-AB1/L-AB1 D-DIX/L-DIX Natural product Efficient synthesis Chiral aziridines