Synthesis of Rigid p-Terphenyl-Linked Carbohydrate Mimetics

M. Kandziora, H.-U. Reissig – 2014

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 provided the corresponding bicyclic 1,2-oxazine derivative that may be regarded as internally protected amino sugar analogue. After subsequent reduction of the carbonyl group, the resulting bicyclic compound was used for Suzuki cross-couplings to form biphenyl aminopyran or p-terphenyl-linked dimers. Hydrogenolysis afforded new unnatural aminosugar mimetics. Zinc in the presence of acid or samarium diiodide were examined for the N–O bond cleavage in order to obtain the rigid p-terphenyl-linked C-glycosyl dimers.

Titel
Synthesis of Rigid p-Terphenyl-Linked Carbohydrate Mimetics
Verfasser
M. Kandziora, H.-U. Reissig
Datum
2014
Kennung
10.3762/bjoc.10.182
Zitierweise
Beilstein J. Org. Chem. 2014, 10, 1749-1758
Art
Text
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