Ontology highlight
ABSTRACT:
SUBMITTER: Kandziora M
PROVIDER: S-EPMC4142845 | biostudies-literature | 2014
REPOSITORIES: biostudies-literature
Beilstein journal of organic chemistry 20140730
An approach to β-D-2-aminotalose- and β-D-2-aminoidose-configured carbohydrate mimetics bearing a phenyl substituent is described. Unnatural divalent rigid p-terphenyl-linked C-aryl glycosides with 2.0 nm dimension are available using Suzuki cross-couplings. The key compound, a p-bromophenyl-substituted 1,2-oxazine, was prepared by a stereoselective [3 + 3]-cyclization of a D-isoascorbic acid-derived (Z)-nitrone and lithiated TMSE-allene. The Lewis acid-induced rearrangement of this heterocycle ...[more]