1075221-29-2Relevant academic research and scientific papers
Regio- and stereoselective lipase-catalysed acylation of methyl α-D-glycopyranosides with fluorinated β-lactams
Sundell, Riku,Siirola, Elina,Kanerva, Liisa T.
, p. 6753 - 6760 (2014)
Burkholderia cepacia lipase (lipase PS-D) catalysed acylation with 3,3-difluoro-4-phenyl-, -thiophen-3-yl- and -4-pyridylazetidin-2-ones was examined for the formation of N-Boc-protected 6-O-acylated sugar-β-amino acid conjugates from methyl α-D-galacto-, -gluco- and mannopyranosides and Boc2O. The 6-O-acylated glycopyranoside-β-amino acid conjugates were isolated and characterized. The low solubility of the gluco- and mannopyranosides and the high reactivity of the pyridylazetidinone restricted product formation. Activation of the β-lactam ring by the presence of fluorine substituents was shown to be necessary for the enzymatic acylation reaction. The (S)-enantiomers of the racemic β-lactam substrates reacted with the sugars. The lipase-catalysed diastereoselective ring-opening of aromatic and hetero-aromatic β-lactams was explored for the formation of β-amino acid conjugates of methyl α-D-glycopyranosides. Potential hydrolytic side-reactions were minimized by a suitable choice of solvent, lipase preparation and the use of molecular sieves.
Synthesis of α,α-difluoro-β-amino esters or gem-difluoro-β-lactams as potential metallocarboxypeptidase inhibitors
Boyer, Nicolas,Gloanec, Philippe,De Nanteuil, Guillaume,Jubault, Philippe,Quirion, Jean-Charles
scheme or table, p. 4277 - 4295 (2009/04/10)
The synthesis of gem-difluorinated β-lactams and gem-difluorinated β-amino acids, each possessing a potential basic functional group, from ethyl bromodifluoroacetate and either imines (for β-lactams) or N-(α-aminoalkyl)benzotriazoles (for β-amino esters) was investigated. A series of these compounds were used for the design of novel metallocarboxypeptidase inhibitors. N-Alkylation and N-acylation of these two versatile scaffolds were carried out, leading to the expected targets in moderate to good yields. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
