Electrochemical O-glycosylation using thioglycosides as glycosyl donors in the presence of a catalytic amount of sodium trifluoromethanesulfonate as a supporting electrolyte

Tanaka, Nobuo; Ohnishi, F; Uchihata, Daisuke; Torii, S.; Nokami, Junzo

doi:10.1016/j.tetlet.2007.08.004

Cited by 35 publications

(13 citation statements)

References 36 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…12 For the effective glycosylation with a sterol, several glycosyl donors have been developed, which are glycosyl halide, 19 glycosyl sulfide 20 and glycosyl trichloroacetimidate. 18,21,25 In our synthesis, 2-O-benzoyl-glycosyl trichloroacetimidates (compound 7, 8 and 9) as the glycosyl donor and Lewis acid as the promoter have been chosen for the stereoselective glycosylation of ergosterol and DHE.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Ergosterol and 5,6-Dihydroergosterol Glycosides and Their Inhibitory Activities on Lipopolysaccharide-Induced Nitric Oxide Production

Lee¹,

Chang²,

Kwon³

et al. 2013

Bulletin of the Korean Chemical Society

View full text Add to dashboard Cite

We have synthesized several glycosyl ergosterols and 5,6-dihydroergosterols (DHE) and examined their effects on production of nitric oxide (NO) and iNOS protein expression in LPS-treated RAW264.7 macrophage cells. Our results showed that DHE derivatives inhibited production of NO and iNOS protein expression more strongly than ergosterol derivative. Especially, DHE-Glc exhibited most potent inhibitory activity without cytotoxicity up to the concentration of 100 µM.

show abstract

Section: Resultsmentioning

confidence: 99%

Synthesis of Ergosterol and 5,6-Dihydroergosterol Glycosides and Their Inhibitory Activities on Lipopolysaccharide-Induced Nitric Oxide Production

Lee¹,

Chang²,

Kwon³

et al. 2013

Bulletin of the Korean Chemical Society

View full text Add to dashboard Cite

show abstract

“…This method was also adapted to aryl thioglycosides, but then glycosylation occurred at a lower oxidation potential. [26][27][28][29] The method presented in this paper is completely different from the previous ones.…”

Section: Contents Lists Available At Sciencedirectmentioning

confidence: 91%

A selective electrochemical method of glycosylation of 3β-hydroxy-Δ5-steroids

Morzycki

Łotowski

Siergiejczyk

et al. 2010

Carbohydrate Research

View full text Add to dashboard Cite

“…A special advantage of this process is that low‐temperature reactions or additives used to remove water from the reaction, such as molecular sieves, are not necessary. Electrochemical O‐glycosylation of primary alcohols with thioglycoside donors have been reported by Nokamia and co‐workers in the presence of a small amount of sodium trifluoromethansulfonate as the supporting electrolyte (Scheme ).…”

Section: Glycosylationsmentioning

confidence: 99%

Chemical O‐Glycosylations: An Overview

2016

View full text Add to dashboard Cite

The development of glycobiology relies on the sources of particular oligosaccharides in their purest forms. As the isolation of the oligosaccharide structures from natural sources is not a reliable option for providing samples with homogeneity, chemical means become pertinent. The growing demand for diverse oligosaccharide structures has prompted the advancement of chemical strategies to stitch sugar molecules with precise stereo‐ and regioselectivity through the formation of glycosidic bonds. This Review will focus on the key developments towards chemical O‐glycosylations in the current century. Synthesis of novel glycosyl donors and acceptors and their unique activation for successful glycosylation are discussed. This Review concludes with a summary of recent developments and comments on future prospects.

show abstract

Electrochemical O-glycosylation using thioglycosides as glycosyl donors in the presence of a catalytic amount of sodium trifluoromethanesulfonate as a supporting electrolyte

Cited by 35 publications

References 36 publications

Synthesis of Ergosterol and 5,6-Dihydroergosterol Glycosides and Their Inhibitory Activities on Lipopolysaccharide-Induced Nitric Oxide Production

Synthesis of Ergosterol and 5,6-Dihydroergosterol Glycosides and Their Inhibitory Activities on Lipopolysaccharide-Induced Nitric Oxide Production

A selective electrochemical method of glycosylation of 3β-hydroxy-Δ5-steroids

Chemical O‐Glycosylations: An Overview

Contact Info

Product

Resources

About