Journal ArticleDOI
High-Yield Syntheses of Tetra-O-benzyl-α-D-glucopyranosyl bromide and Tetra-O-pivaloyl-α-D-glucopyranosyl bromide and their Advantage in the Koenigs-Knorr Reaction
TLDR
Several improved approaches for the preparation of tetra-O-benzyl-α-D-glucopyranosyl bromide and tetra O-pivaloyl-α,D-GLUCOPYRANOSYL Bromide are discussed in this article.Abstract:
Several improved approaches for the preparation of tetra-O-benzyl-α-D-glucopyranosyl bromide and tetra-O-pivaloyl-α-D-glucopyranosyl bromide are discussed. The importance of these compounds, which are useful glycosyl donors, was demonstrated by successful preparation of cholesteryl glucopyranosides in an almost neutral medium without the formation of orthoesters. In addition, accurate 1H and 13C NMR resonance assignments of the synthesized cholesteryl glycosides were performed by 2D NMR spectroscopy.read more
Citations
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New Method for Regioselective Glycosylation Employing Saccharide Oxyanions
Martin Matwiejuk,Joachim Thiem +1 more
TL;DR: In this paper, the prior activation of acceptor hydroxy groups for selective glycosidic bond formation, was investigated to give complex oligosaccharides, and the scope of the methodology was extended with different perbenzylated glycosyl donors.
Journal ArticleDOI
β-Selective C-Glycosylation and its Application in the Synthesis of Scleropentaside A.
TL;DR: A Corey-Seebach umpolung reaction as the key step in the synthesis of scleropentaside A and analogues enables the β-selective construction of the anomeric C-C bond starting from unprotected carbohydrates in only four steps, which is highly atom-efficient and avoids the use of toxic heavy metals.
Journal ArticleDOI
Asymmetric synthesis of cyclo-archaeol and β-glucosyl cyclo-archaeol.
Catalina Ferrer,Peter Fodran,Santiago Barroso,Robert A. Gibson,Ellen C. Hopmans,Jaap S. Sinninghe Damsté,Stefan Schouten,Adriaan J. Minnaard +7 more
TL;DR: An efficient asymmetric synthesis of cyclo-archaeol and β-glucosyl Cyclo-Archaeol is presented employing catalytic asymmetric conjugate addition and catalytic epoxide ring opening as the key steps.
Journal ArticleDOI
Synthesis and Biological Evaluation of the Novel Growth Inhibitor Streptol Glucoside, Isolated from an Obligate Plant Symbiont.
Chien-Chi Hsiao,Simon Sieber,Antri Georgiou,Aurélien Bailly,Despina Emmanouilidou,Aurélien Carlier,Leo Eberl,Karl Gademann +7 more
TL;DR: Results provide compelling evidence that the glucosylation of (+)-streptol protects the plant host against the growth inhibitory effect of the compound, which might constitute a molecular cornerstone for this successful plant-bacteria symbiosis.
References
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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
Halide ion catalyzed glycosidation reactions. Syntheses of .alpha.-linked disaccharides
Journal ArticleDOI
Chemistry of the glycosidic linkage. An efficient synthesis of 1,2-trans-di-saccharides
Stephen Hanessian,Joseph Banoub +1 more
Journal ArticleDOI
Exploring the Mechanism of Neighboring Group Assisted Glycosylation Reactions
TL;DR: Glycosyl donors based on the 2,6-di-O-acyl-3,4-Oisopropylidene-d-galactopyranosyl-(leaving group) structure have been shown experimentally to have a high propensity for giving acyl transfer to the alcohol nucleophile as major side products in the glycosylation reaction.
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