STRATEGY AND PREPARATION OF SOME BUILDING BLOCKS FOR SYNTHESIS OF BRANCHED OLIGOSACCHARIDES

• Main Author: V. A. Bacherikov
• Format: Article
• Language: English
• Published: Odessa I. I. Mechnikov National University 2015-06-01
• Series: Vìsnik Odesʹkogo Nacìonalʹnogo Unìversitetu: Hìmìâ
• Subjects: синтетичні блоки, захищені моносахариди, β-(1,3)-D-глюкани, синтез
• Online Access: http://heraldchem.onu.edu.ua/article/view/44553

The importance of the role of oligosaccharides in biological processes relating to immunology, virology, cancer, antibiotic action has heightened the interest in accessibility and study of methods of their synthesis, including one-pot glycosidation, solid-phase synthesis, remote glycosilation and armed/disarmed glycosidation. Article discuss modern strategy of a glycoside bond formations based on the knowledge that a large disparity between the reactivities of the different glycosyl donors can be achieved by varying the protecting group and electrondonating or withdrawing character of the leaving group within the given classes of glycosyl donor. The synthetic approach designed in such pathway that the particular combination of protecting groups and anomeric substituents on sugar components would be selected. Several modern pathways for the design and the synthesis of branched oligosaccharides using various reactivity protective groups were discussed. A synthetic plan in which chosen protecting groups – acetyl (Ac), benzyl (Bn), 2-naphtyl (2-Naph), p-methoxybenzyl (PMB) and p-chlorobenzyl  (p-ClBn) can be further selectively removed in high yields was represent in the article.  Among the commonly used leaving groups in donor molecules thioglycosides were chosen as universal building block because they are stable under most reaction conditions often using for the construction building blocks of β-(1,3)-D-glucans. The methods of synthesis of some promising synthetic blocks for production of the corresponding branched oligo-derivatives were also outlined.