Ionic‐Liquid Tag with Multiple Functions in Electrochemical Glycosylation

Nokami, Toshiki; Sasaki, Norihiko; Isoda, Yuta; Itoh, Toshiyuki

doi:10.1002/celc.201600311

Cited by 11 publications

(3 citation statements)

References 37 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…This method was successfully applied to the synthesis of protected potential N,N,N-trimethyl-D-glucosaminyl-(TMG-) chitotriomycin precursors (Scheme 37). 95 Nokami, Itoh, and co-workers 96 developed a benzyl ethertype ionic-liquid tag (IL tag 97 ) for electrochemical glycosylation based on the glycosyl triflate pool method (Scheme 38). The electrochemical glycosylation of tagged thioglycosides gives αisomers as major products, indicating that the stereoselectivity is opposite to that of thioglycosides without the IL tag.…”

Section: Stabilized Glycosyl Cationsmentioning

confidence: 99%

Electrogenerated Cationic Reactive Intermediates: The Pool Method and Further Advances

2017

View full text Add to dashboard Cite

Electrochemistry serves as a powerful method for generating reactive intermediates, such as organic cations. In general, there are two ways to use reactive intermediates for chemical reactions: (1) generation in the presence of a reaction partner and (2) generation in the absence of a reaction partner with accumulation in solution as a "pool" followed by reaction with a subsequently added reaction partner. The former approach is more popular because reactive intermediates are usually short-lived transient species, but the latter method is more flexible and versatile. This review focuses on the latter approach and provides a concise overview of the current methods for the generation and accumulation of cationic reactive intermediates as a pool using modern techniques of electrochemistry and their reactions with subsequently added nucleophilic reaction partners.

show abstract

Section: Stabilized Glycosyl Cationsmentioning

confidence: 99%

Electrogenerated Cationic Reactive Intermediates: The Pool Method and Further Advances

2017

View full text Add to dashboard Cite

show abstract

“…N -Phenyl trifluoroacetimidate (PTFAI) , and regenerative glycosylation using in situ generated 3,3-difluoro-3H-indol-2-yl (OFox), ortho -(methyltosylaminoethynyl)benzyl glycosides, glycosyl o -alkynylbenzoate (ABz), − propargyl glycosides, propargyl orthoesters, and alkynyl carbonates, 2-(2-propylsulfinyl)benzyl (PSB)/S-2-(2-propylsulfinyl)benzyl (SPSP) glycosides methods, , phenyl glycosides, − o -( p -methoxyphenylethynyl)phenyl (MPEP) glycosides, hydroxybenzotriazolyl glycosides, and glycosyl isoquinoline-1-carboxylate . In the past few years, novel promoters and conditions have been introduced for the activation of existing donors. − Recently, a β-selective ring closing glycosylation via a nonglycosylating pathway was also described …”

Section: Glycosylationmentioning

confidence: 99%

“One-Pot” Protection, Glycosylation, and Protection–Glycosylation Strategies of Carbohydrates

et al. 2018

View full text Add to dashboard Cite

Carbohydrates, which are ubiquitously distributed throughout the three domains of life, play significant roles in a variety of vital biological processes. Access to unique and homogeneous carbohydrate materials is important to understand their physical properties, biological functions, and disease-related features. It is difficult to isolate carbohydrates in acceptable purity and amounts from natural sources. Therefore, complex saccharides with well-defined structures are often most conviently accessed through chemical syntheses. Two major hurdles, regioselective protection and stereoselective glycosylation, are faced by carbohydrate chemists in synthesizing these highly complicated molecules. Over the past few years, there has been a radical change in tackling these problems and speeding up the synthesis of oligosaccharides. This is largely due to the development of one-pot protection, one-pot glycosylation, and one-pot protection-glycosylation protocols and streamlined approaches to orthogonally protected building blocks, including those from rare sugars, that can be used in glycan coupling. In addition, new automated strategies for oligosaccharide syntheses have been reported not only for program-controlled assembly on solid support but also by the stepwise glycosylation in solution phase. As a result, various sugar molecules with highly complex, large structures could be successfully synthesized. To summarize these recent advances, this review describes the methodologies for one-pot protection and their one-pot glycosylation into the complex glycans and the chronological developments associated with automated syntheses of oligosaccharides.

show abstract

“…Ionic liquid tags (IL‐tags), which are introduced as protecting groups of carbohydrate hydroxyl moieties, are also useful for electrochemical glycosylation [27,28] . They work not only as a separation tag, but also as electrolyte and stereo‐directing group.…”

Section: Electrochemical Assembly For the Synthesis Of Oligosaccharidesmentioning

confidence: 99%

Electrochemical Assembly for Synthesis of Middle‐Sized Organic Molecules

Shibuya

Nokami

2021

The Chemical Record

Self Cite

View full text Add to dashboard Cite

Electrochemical methods offer a powerful, reliable, and environmentally benign approach for the synthesis of small organic molecules, and such methods are useful not only for the transformation of small molecules, but also for the preparation of oligomers and polymers. Electrochemical assembly is a concept that allows structurally well‐defined middle‐sized organic molecules to be synthesized by applying electrochemical methods. The preparation of dendrimers, dendronized polymers, and oligosaccharides are introduced as examples of such an approach. Automated electrochemical assembly of oligosaccharides is also demonstrated using the electrochemical synthesizer developed by our group.

show abstract

Ionic‐Liquid Tag with Multiple Functions in Electrochemical Glycosylation

Cited by 11 publications

References 37 publications

Electrogenerated Cationic Reactive Intermediates: The Pool Method and Further Advances

Electrogenerated Cationic Reactive Intermediates: The Pool Method and Further Advances

“One-Pot” Protection, Glycosylation, and Protection–Glycosylation Strategies of Carbohydrates

Electrochemical Assembly for Synthesis of Middle‐Sized Organic Molecules

Contact Info

Product

Resources

About