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Molecules  2008 

A Novel Synthetic Approach to C-Glycosyl-D- and L-Alanines

DOI: 10.3390/molecules13123171

Keywords: C-Glycosyl amino acids, C-Glycosyl alanine, [3, 3]-Sigmatropic rearrangements, Microwave irradiation, X-ray diffraction

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Abstract:

C-Glycosyl-(S)- and (R)-alanines 12a and 12b were synthesized from the known β-C-glycoside 1. The nitrogen function was introduced by aza-Claisen rearrangement of the allylic thiocyanate 7, derived from the corresponding alcohol 6. The absolute configuration of the newly created chiral carbon center (C-3) was assigned by X-ray diffraction analysis of the intermediate 3(S)-isothiocyanato-D-glycero-D-galacto-decose 8a.

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