Journal ArticleDOI
Thio-sugars. Part 5: From d-glucal to 3-deoxy-(1→2)-2-S-thiodisaccharides through isolevoglucosenone—a simple approach
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TLDR
In this paper, a new synthesis of isolevoglucosenone and its stereoselective functionalization into 3-deoxy-(1-2)-2-S-thiodisaccharides is described.Abstract:
A new synthesis of isolevoglucosenone and its stereoselective functionalization into 3-deoxy-(1-2)-2-S-thiodisaccharides is described. The base-catalyzed conjugate addition of 1-thiosugars to isolevoglucosenone followed by the reduction of the C-4 keto function constitute a new two-step general approach to these classes of biologically important thio-sugars.read more
Citations
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Synthetic Routes to Thiooligosaccharides and Thioglycopeptides
Journal ArticleDOI
Thiosugars: new perspectives regarding availability and potential biochemical and medicinal applications.
TL;DR: New developments and representative examples of functionalized thiosugar prototypes as potential new targets are presented in this mini review.
Journal ArticleDOI
Levoglucosenone and Its New Applications: Valorization of Cellulose Residues
María Betina Comba,Yi-hsuan Tsai,Ariel M. Sarotti,Maria Ines Mangione,Alejandra G. Suárez,Rolando A. Spanevello +5 more
TL;DR: The selective pyrolytic conversion of cellulose or cellulose-containing materials produces levoglucosenone, a highly functionalized chiral structure that has been used as a template for the synthesis of key intermediates of biologically active products and for the preparation of chiral auxiliaries, catalysts, and organocatalysts for their application in asymmetric synthesis as mentioned in this paper.
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Thio-sugars VII. Effect of 3-deoxy-4-S-(β-d-gluco- and β-d-galactopyranosyl)-4-thiodisaccharides and their sulfoxides and sulfones on the viability and growth of selected murine and human tumor cell lines
TL;DR: Results indicate that deoxythio-disaccharide analogs generated by functionalization of the universal chiral precursor levoglucosenone may have cytotoxic properties and therapeutic potential as anticancer agents.
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Synthesis of Multivalent Glycoclusters from 1-Thio-β-d-galactose and Their Inhibitory Activity against the β-Galactosidase from E. coli
TL;DR: The use of hydrophilic carbohydrate scaffolds for the synthesis of multivalent galactosides represents an interesting approach to improve their pharmacokinetics and bioavailability and the presence of the thioglycosidic bond will improve their stability in biological fluids.
References
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Synthesis of methyl 2,3-dideoxy-DL-alk-2-enopyranosides from furan compounds
TL;DR: In this article, a method of converting furan derivatives via 2,3-dideoxy-DL -alk-2-enopyranos-4-uloses, a new class of sugar compounds, into methyl 2, 3-D-Dideoxy DL -alk 2-ENOPyranosides is described.
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Some reactions of levoglucosenone
TL;DR: The role of the major variables in the pyrolytic production of levoglucosenone from acid-treated cellulose and paper has been established as discussed by the authors, and reduction, oxidation, acid-and base-catalyzed addition, acetolysis, and rearrangement reactions of this product have been investigated.
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A Convenient, Highly Efficient One-Pot Preparation of Peracetylated Glycals From Reducing Sugars
TL;DR: In this article, a one-pot, three-step procedure was developed for the synthesis of peracetylated glycal derivatives from various reducing sugars including D-glucose, D-galactose, L-rhamnose and L-arabinose.
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Thiosugars II. A novel approach to thiodisaccharides The synthesis of 3-deoxy-4-thiocellobiose from levoglucosenone
TL;DR: An expeditious methodology for the synthesis of β-(1 → 4)-3-deoxythiodisaccharides (3- deoxythiocellobiose) has been developed and is based on the stereoselective Michael addition of 2,3,4,6-tetra-O-acetyl-1-thio-β-d-glucose to levoglucosenone.
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Synthesis of p-nitrobenzyl and p-nitrophenyl 1-trioglycopyranosides
TL;DR: A facile preparation of O-acylated p-nitrophenyl 1-thioglycopyranosides was achieved by condensing the appropriate glycosyl halide with sodium p-Nitrobenzenethioxide in N,N-dimethylformamide.