Abstract
A short synthetic route to stereoselective access to C-glycosyl-aminoethyl sulfide derivatives has been developed through the reaction of tributhyltin derivatives of glycals with aziridinecarboaldehyde and the regioselective ring opening of a chiral aziridine with thiophenol. The absolute configurations of the resulting diastereoisomers were determined by 1H NMR spectroscopy.
Highlights
Developed in recent years, asymmetric synthesis has proved to be a powerful tool in the synthesis of drugs and natural products as well as in the transformation of readily available simple compounds into chiral building blocks used for the synthesis of more complex connections [1–3]
Research conducted at the borderline of chemistry, biology and medicine indicates an urgent need for the synthesis of natural and non-natural saccharides and glycoconjugates of well-defined structure and composition
Due to their participation in many important biochemical processes, the increasing interest in them is justified. These compounds can serve as probes in research aimed at elucidating complex functions that carbohydrates play at the molecular level in living organisms, and can be used in the synthesis of new drugs based on carbohydrates [4–14]
Summary
Developed in recent years, asymmetric synthesis has proved to be a powerful tool in the synthesis of drugs and natural products as well as in the transformation of readily available simple compounds into chiral building blocks used for the synthesis of more complex connections [1–3]. Sugars are the most readily available raw materials, they were long considered of little use due to the presence of polar functional groups. It turns out th–t the structure is a great advantage, enabling wide-ranging possibilities of modification, making them very useful synthetic tools. Research conducted at the borderline of chemistry, biology and medicine indicates an urgent need for the synthesis of natural and non-natural saccharides and glycoconjugates of well-defined structure and composition Due to their participation in many important biochemical processes, the increasing interest in them is justified. Considering our previous results on carbohydrate chemistry [51–58] and based on our experience in synthesis and catalytic activity in the asymmetric synthesis of chiral aziridines [59–65], we decided to couple aziridines to glycals with D-gluco and D-galacto configurations via C-glycosidic bonding, with the final formation of C-glycosyl-aminoethyl sulfide derivatives
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