Book ChapterDOI
Thioglycosides as glycosyl donors in oligosaccharide synthesis.
TLDR
This chapter analyzes the importance of thioclycosides as the glycosyl donors in oligosaccharide synthesis and the transfer of the Armed–Disarmed concept to thioglycoside Glycosylation reactions is elaborated.Abstract:
Publisher Summary This chapter analyzes the importance of thioclycosides as the glycosyl donors in oligosaccharide synthesis. The presence and biological importance of oligosaccharide structures, usually as the components of glycolipids and glycoproteins, in bacterial capsular and cell-wall polysaccharides, in mammalian cell membranes, in cytoplasm, and in extra-cellular fluids are well documented. Acylated glycosyl thiocyanates are made by the treatment of acylated glycopyranosyl halides with potassium thiocyanate. An attractive feature of thioglycosides as the glycosyl donors in oligosaccharide synthesis is that they are readily converted into all of the other glycosyl donors. The glycosyl bromide can also be converted into a 4-pentenyl glycoside, which becomes a glycosyl donor by promotion with an iodonium compound. Tris(4-bromophenyl)ammoniurnyl hexachloroantimonate (TBPA) differs from the other promoters in the context that its cation is a radical and produces radical cationic sulfonium ions such as glycosylating species from thioglycosides. In acetonitrile as solvent, and with a nonparticipating 2-substituent in the glycosyl donor, 1,2-trans glycosides are formed as a result of solvent participant. The transfer of the Armed–Disarmed concept to thioglycoside glycosylation reactions is also elaborated in the chapter.read more
Citations
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PatentDOI
Programmable one-pot oligosaccharide synthesis
TL;DR: In this article, the reactivity of a number of p-methylphenyl thioglycoside (STol) donors which are either fully protected or have one hydroxyl group exposed has been quantitatively determined by HPLC in conjunction with the development of a broadly applicable approach for a facile one-pot synthesis of oligosaccharides.
Journal ArticleDOI
Toward automated synthesis of oligosaccharides and glycoproteins.
Pamela Sears,Chi-Huey Wong +1 more
TL;DR: Recent advances in carbohydrate synthesis are described, with particular focus on developments that have potential application to the automated synthesis of oligosaccharides, glycopeptides, and glycoproteins.
Journal ArticleDOI
Glycosylated Porphyrins, Phthalocyanines, and Other Porphyrinoids for Diagnostics and Therapeutics.
Sunaina Singh,Amit Aggarwal,N. V. S. Dinesh K. Bhupathiraju,Gianluca Arianna,Kirran Tiwari,Charles Michael Drain,Charles Michael Drain +6 more
TL;DR: This paper presents a meta-analyses of the prophylactic and non-prolific approaches used in the treatment of central nervous system disorders and their applications in women and young people.
Journal ArticleDOI
Thioglycosides in sequential glycosylation strategies
Jeroen D. C. Codée,Remy E. J. N. Litjens,Leendert J. van den Bos,Herman S. Overkleeft,Gijsbert A. van der Marel +4 more
TL;DR: This tutorial review surveys the use of thioglycosides in the development of sequential glycosylation methodologies, with a focus on chemoselective, orthogonal and iterative glycosidic bond formation strategies reported since the beginning of this century.
Journal ArticleDOI
Chemical glycosylation in the synthesis of glycoconjugate antitumour vaccines
Danica P. Galonić,David Y. Gin +1 more
TL;DR: This work has shown that the use of both state-of-the-art and emerging glycosylation technologies has led to significant advances in this field, allowing the clinical exploration of carbohydrate-based antigens in the treatment of cancer.
References
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Journal ArticleDOI
New Methods for the Synthesis of Glycosides and Oligosaccharides—Are There Alternatives to the Koenigs‐Knorr Method? [New Synthetic Methods (56)]
TL;DR: Emphasis is placed on glycoside and saccharide formation by 1-O-alkylation, on the trichloroacetimidate method, and on activation through the formation of glycosylsulfonium salts and Glycosyl fluorides.
Journal ArticleDOI
Recent progress in O-glycosylation methods and its application to natural products synthesis
Kazunobu Toshima,Kuniaki Tatsuta +1 more
Journal ArticleDOI
Advances in Selective Chemical Syntheses of Complex Oligosaccharides
TL;DR: A wide variety of complex oligosaccharides has now been made accessible as a result of methodological improvements in the sphere of chemical synthesis, which can be used for the study of conformations and interactions with protein-receptor molecules.
Journal ArticleDOI
Iodonium ion promoted reactions at the anomeric centre. II An efficient thioglycoside mediated approach toward the formation of 1,2-trans linked glycosides and glycosidic esters
TL;DR: NIS together with a catalytic amount of trifluoromethanesulfonic acid proved to be very convenient for the rapid, high-yielding and stereoselective (1,2-trans) glycosidation of esterified thioglycosides with glycosyl acceptors.
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