Potenti, Simone; Spada, Lorenzo; Fuse, Marco; Mancini, Giordano; Gualandi, Andrea; Leonardi, Costanza; Cozzi, Pier Giorgio; Puzzarini, Cristina; Barone, Vincenzo published an article in 2021. The article was titled 《4-Fluoro-Threonine: From Diastereoselective Synthesis to pH-Dependent Conformational Equilibrium in Aqueous Solution》, and you may find the article in ACS Omega.Name: 2-(Benzyloxy)acetaldehyde The information in the text is summarized as follows:
4-Fluorothreonine, the only fluoro amino acid of natural origin discovered so far, is an interesting target for both synthetic and theor. investigations. In this work, we lay the foundation for spectroscopic characterization of 4-fluorothreonine. First, we report a diastereoselective synthetic route, which is suitable to produce synthetic material for exptl. characterization. The addition of the com. available Et isocyanoacetate to benzyloxyacetaldehyde led to the corresponding benzyloxy-oxazoline, which was hydrolyzed and transformed into Et (4S*,5S*)-5-hydroxymethyl-2-oxo-4-oxazolidinecarboxylate in a few steps. Fluorination with diethylamino sulfur trifluoride (DAST) afforded Et (4S*,5S*)-5-fluoromethyl-2-oxo-4-oxazolidinecarboxylate, which was deprotected to give the desired diastereomerically pure 4-fluorothreonine, in 8-10% overall yield. With the synthetic material in our hands, acid-base titrations have been carried out to determine acid dissociation constants and the isoelec. point, which is the testing ground for the theor. anal. We have used machine learning coupled with quantum chem. at the state-of-the-art to analyze the conformational space of 4-fluoro-threonine, with the aim of gaining insights from the comparison of computational and exptl. results. Indeed, we have demonstrated that our approach, which couples a last-generation double-hybrid d. functional including empirical dispersion contributions with a model combining explicit first-shell mols. and a polarizable continuum for describing solvent effects, provides results and trends in remarkable agreement with experiments Finally, the conformational anal. applied to fluoro amino acids represents an interesting study for the effect of fluorine on the stability and population of conformers. After reading the article, we found that the author used 2-(Benzyloxy)acetaldehyde(cas: 60656-87-3Name: 2-(Benzyloxy)acetaldehyde)
2-(Benzyloxy)acetaldehyde(cas: 60656-87-3) is a non-natural aldehyde. It undergoes enantioselective Mukaiyama aldol reaction with silylketene acetal nucleophiles in the presence of C2-symmetric bis(oxazolinyl)pyridine Cu(II) complex (catalyst).Name: 2-(Benzyloxy)acetaldehyde
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