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

doi:10.3390/molecules13123171

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

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

Miroslava Martinková^1,* , Jozef Gonda¹, Jana Raschmanová¹, Alexandra Novodomská¹, Jozef Kožíšek² and Lucia Perasinová²

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; in revised form: 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

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MDPI and ACS Style

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.

AMA Style

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(12):3171-3183.

Chicago/Turabian Style

Martinková, Miroslava; Gonda, Jozef; Raschmanová, Jana; Novodomská, Alexandra; Kožíšek, Jozef; Perasinová, Lucia. 2008. "A Novel Synthetic Approach to C-Glycosyl-D- and L-Alanines." Molecules 13, no. 12: 3171-3183.

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