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• W2103248866 abstract "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." @default.
• W2103248866 created "2016-06-24" @default.
• W2103248866 creator A5033234332 @default.
• W2103248866 creator A5081413658 @default.
• W2103248866 date "2014-07-30" @default.
• W2103248866 modified "2023-10-17" @default.
• W2103248866 title "Synthesis of rigid <i>p</i>-terphenyl-linked carbohydrate mimetics" @default.
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• W2103248866 doi "https://doi.org/10.3762/bjoc.10.182" @default.
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