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Molecules 2008, 13(12), 3171-3183; doi:10.3390/molecules13123171
Article

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

1,* , 1
, 1
, 1
, 2
 and 2
1 Institute of Chemical Sciences, Department of Organic Chemistry, P. J. Šafárik University, Moyzesova 11, SK-040 01 Košice, Slovak Republic 2 Faculty of Chemical and Food Technology, Department of Physical Chemistry, Slovak University of Technology, Radlinského 9, SK-812 37 Bratislava, Slovak Republic
* Author to whom correspondence should be addressed.
Received: 16 November 2008 / Revised: 10 December 2008 / Accepted: 11 December 2008 / Published: 15 December 2008
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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.
Keywords: C-Glycosyl amino acids; C-Glycosyl alanine; [3; 3]-Sigmatropic rearrangements; Microwave irradiation; X-ray diffraction C-Glycosyl amino acids; C-Glycosyl alanine; [3; 3]-Sigmatropic rearrangements; Microwave irradiation; X-ray diffraction
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Martinková, M.; Gonda, J.; Raschmanová, J.; Novodomská, A.; Kožíšek, J.; Perasinová, L. A Novel Synthetic Approach to C-Glycosyl-D- and L-Alanines. Molecules 2008, 13, 3171-3183.

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