A novel synthetic approach to C-glycosyl-D- and L-alanines.
C-Glycosyl-(S)- and (R)-alanines 12a and 12b were synthesized from the known beta-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.
Martinková
Miroslava
M
Institute of Chemical Sciences, Department of Organic Chemistry, P. J. Safárik University, Moyzesova 11, SK-040 01 Kosice, Slovak Republic. miroslava.martinkova@upjs.sk
Gonda
Jozef
J
Raschmanová
Jana
J
Novodomská
Alexandra
A
Kozísek
Jozef
J
Perasinová
Lucia
L
D000409:Alanine / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular
D006027:Glycosides; D000409:Alanine