%0 Journal Article
%T A Novel Synthetic Approach to C-Glycosyl-D- and L-Alanines
%A Miroslava Martinkov¨¢
%A Jozef Gonda
%A Jana Raschmanov¨¢
%A Alexandra Novodomsk¨¢
%A Jozef Ko£¿¨ª£¿ek
%A Lucia Perasinov¨¢
%J Molecules
%D 2008
%I MDPI AG
%R 10.3390/molecules13123171
%X C-Glycosyl-(S)- and (R)-alanines 12a and 12b were synthesized from the known ¦Â-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.
%K C-Glycosyl amino acids
%K C-Glycosyl alanine
%K [3
%K 3]-Sigmatropic rearrangements
%K Microwave irradiation
%K X-ray diffraction
%U http://www.mdpi.com/1420-3049/13/12/3171