The Evaluation of Catalysts Generated from Lewis Acids and Silver Perchlorate in a Highly Stereoselective Glycosylation of 1-<i>O</i>-Acetyl-D-glucose

Mukaiyama, Teruaki; Katsurada, Manabu; Takashima, Tohru

doi:10.1246/cl.1991.985

Cited by 45 publications

(19 citation statements)

References 11 publications

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“…Various glucosylation methods have been developed since the classical KoenigsKnorr synthesis. 3 Usually, these procedures require either an activated glucosyl donor, e.g., a glucosyl halide, 4,5 trimethylsilyl 2,3,4,6-tetra-O-acetyl-D-glucopyranoside, 6 or a trichloroacetimidate, 7,8 a glucosyl acceptor with a good leaving group [9][10][11] or a precious metal catalyst. 12,13 Glucosylation can also be performed enzymically; 14 the unprotected monosaccharide is derivatized in a water-poor system using the glucosyl acceptor (e.g., allyl or benzyl alcohol) as the solvent.…”

Section: Introductionmentioning

confidence: 99%

Reliable method for the synthesis of aryl β-D-glucopyranosides, using boron trifluoride–diethyl ether as catalyst

Smits¹,

Engberts²,

Kellogg³

et al. 1996

J. Chem. Soc., Perkin Trans. 1

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Reliable method for the synthesis of aryl β-D-glucopyranosides, using boron trifluoride-diethyl ether as catalyst Smits, Elly; Engberts, Jan; Kellogg, Richard M.; Doren, Henk A. van Take-down policy If you believe that this document breaches copyright please contact us providing details, and we will remove access to the work immediately and investigate your claim.Downloaded from the University of Groningen/UMCG research database (Pure): http://www.rug.nl/research/portal. For technical reasons the number of authors shown on this cover page is limited to 10 maximum. Stereospecific formation of aryl 2,3,4,6-tetra-O-acetyl-β β-D-glucopyranosides was achieved by reaction of penta-O-acetyl-β β-D-glucose 1 with substituted phenols in the presence of boron trifluoride. Yields of the purified products varied from 52-85%. Benzyl alcohol could also be glucosylated using similar conditions. All products were purified by crystallization from ethanol. The purity and the anomeric configuration of the products were determined by means of 1 H and 13 C NMR spectroscopy, melting points and optical rotation.

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Section: Introductionmentioning

confidence: 99%

Reliable method for the synthesis of aryl β-D-glucopyranosides, using boron trifluoride–diethyl ether as catalyst

Smits¹,

Engberts²,

Kellogg³

et al. 1996

J. Chem. Soc., Perkin Trans. 1

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“…Considering that these alternate, but similar reaction pathways would introduce significant complexity into our model, we chose to combine 4 and 5 . We did, however, find that the diastereoselectivity of the reaction was exquisitely sensitive to the solvent, with acetonitrile being optimal but insensitive to Lewis acid structure. , This may suggest the importance of an anomeric nitrilium ion in selectivity, but no detailed studies were pursued to identify this intermediate. The diastereoselectivity of the reaction is likely a result of the stereoelectronic influence of the thioether at C2, as suggested by Roush and co-workers, rather than of an episulfonium ion …”

mentioning

confidence: 86%

Follow the Silyl Cation: Insights into the Vorbrüggen Reaction

Beutner

Bultman

Cohen

et al. 2019

Org. Process Res. Dev.

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To succeed in the development of a mechanistic model for the Vorbruggen reaction of thymine with an advanced furanose intermediate, a range of spectroscopic techniques were applied and found essential to understanding kinetically relevant, yet nonisolable, silylated reaction intermediates. Understanding of the dynamic nature of the interaction of trimethylsilyl trifluoromethanesulfonate with these functionally dense substrates allowed for the accurate prediction and straightforward explanation of the relationship between process parameters and the levels of key impurities.

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“…Glycosylation of M24 with M25 was promoted by SnCl 3 ClO 4 , which was generated in situ from SnCl 4 and AgClO 4 . Each glycosylation cycle took five steps from M23 : two steps each for the synthesis of the donor and acceptor, as well as the glycosylation reaction.…”

Section: Chemical Synthesis Of Amphiphilic Pmpssmentioning

confidence: 99%

Amphiphilic Cytosolic Glycans from Mycobacteria: Occurrence, Lipid‐Binding Properties, Biosynthesis, and Synthesis

Lowary

2013

Biopolymers

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Polymethylated polysaccharides (PMPSs), glycans composed of 10-20 carbohydrate residues the majority of which carry a single methyl group, are produced by some mycobacterial species. O-Methylation thus occurs on 20-30% of all the hydroxyl groups within the molecule, rendering them amphiphilic. A property of PMPSs is their ability to form high-affinity complexes with fatty acids and their derivatives, suggesting a role in mycobacterial fatty acid biosynthesis. However, direct evidence for their in vivo function is still lacking. Over the past several decades the lipid-binding properties, biosynthesis, and chemical synthesis of PMPSs have been explored and this review will provide an overview of progress made in these areas.

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The Evaluation of Catalysts Generated from Lewis Acids and Silver Perchlorate in a Highly Stereoselective Glycosylation of 1-O-Acetyl-D-glucose

Abstract: A catalytic cycle was effectively performed in highly stereoselective glycosylation of 1-O-acetyl-D-glucose by using active species generated from respective combinations of Lewis acids (SnCl4, GeCl4, SiCl4, GaCl3, InCl3, and HfCl4) and silver perchlorate.

Cited by 45 publications

References 11 publications

Reliable method for the synthesis of aryl β-D-glucopyranosides, using boron trifluoride–diethyl ether as catalyst

Reliable method for the synthesis of aryl β-D-glucopyranosides, using boron trifluoride–diethyl ether as catalyst

Follow the Silyl Cation: Insights into the Vorbrüggen Reaction

Amphiphilic Cytosolic Glycans from Mycobacteria: Occurrence, Lipid‐Binding Properties, Biosynthesis, and Synthesis

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