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