Total synthesis of TMG-chitotriomycin based on an automated electrochemical assembly of a disaccharide building block

Isoda, Yuta; Sasaki, Norihiko; Kitamura, Kei; Takahashi, Shuji; Manmode, Sujit; Takeda-Okuda, Naoko; Tamura, Jun’ichi; Nokami, Toshiki; Itoh, Toshiyuki

doi:10.3762/bjoc.13.93

Cited by 33 publications

(12 citation statements)

References 30 publications

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“…To demonstrate the synthetic utility of the method, total synthesis of biologically active oligosaccharides TMG‐chitotriomycin [22–24] and Myc‐IV (C16:0, S) was carried out [25] (Figure 11). Although their tetrasaccharide precursors differ, automated electrochemical assembly for the synthesis of tetrasaccharide precursors 30 a and 30 b started from the same disaccharide 31 as a building block.…”

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

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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.

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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

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“…Another recent hot topic in electroglycosylation would be its integration with automation. Itoh, Nokami, and coworkers reported their pioneering work on automated electrochemical assembly of carbohydrate building blocks (3), especially for the synthesis of a potential precursor of TMG-chitotriomycin tetrasaccharide (19) and a GPI anchor core trisaccharide (20). These works were achieved by the rational optimization of carbohydrate building blocks based on DFT calculation, and the scrutinized oxidation potentials.…”

Section: E116mentioning

confidence: 99%

Current Tools for Chemical Glycosylation: Where Are We Now?

Karak

Animeshchandra²,

Torikai

2021

TIGG

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Glycosylation procedure has long been categorized to one of the most delicate synthetic techniques in the field of organic chemistry, since it requires extremely dry and mild conditions, to prevent the decomposition of substrates, intermediates, and products as well as to activate only appropriate donor species. Although chemists have made great efforts to overcome the difficulty by brushing up their skills to carry out moisture-sensitive reactions and by developing numbers of acid-promoted glycosylation chemistry, there are still troublesome cases that cannot be addressed by human hands. To circumvent this dead-end situation, chemists turned their attention from training their own skills to the development of machinery which can conduct operations that human cannot. In this review, we introduced tools, currently applied and/or developed to facilitate chemical glycosylation reactions. We focused on brand-new results using electrochemical and microfluidic machinery, as well as a simple but useful apparatus, which have never been reviewed yet.Although the precise control of the electrochemical conditions is not an easy task since each glycosyl donor can show different oxidation potentials by changing electrolytes, solvents, temperature, and techniques etc., this methodology is still an efficient synthetic tool to develop an automated synthesizer for complex oligosaccharides.Among various glycosyl donors, thioglycosides have played the most important roles in electro-glycosylation because of their high reactivity of the single electron transfer. Inspired by the out-GLYCOREVIEW

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“…During our study of electrochemical glycosylation, we developed automated electrochemical assembly a method for the automated electrochemical solution‐phase synthesis of oligosaccharides. The method has already been successfully applied to the synthesis of linear oligoglucosamines, TMG‐Chitotriomycin, GPI anchor trisaccharides and 1,3‐1,6‐β‐linked oligoglucosides . Thus, we envisioned that precursors of cyclic oligosaccharides, especially oligoglucosamines, could also be readily prepared using this method, and that subsequent electrochemical glycosylation might be an alternative method for the chemical and enzymatic synthesis of cyclic oligosaccharides.…”

Section: Optimization Of Monosaccharide Terminal Building Blockmentioning

confidence: 99%

Electrochemical Glycosylation as an Enabling Tool for the Stereoselective Synthesis of Cyclic Oligosaccharides

et al. 2019

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Electrochemical glycosylation of a linear oligosaccharide with a protecting‐group‐free primary hydroxyl group afforded cyclic oligo‐saccharides, up to hexasaccharides, in high yields. Precursors of the cyclic oligosaccharides were prepared by automated electro‐chemical assembly‐a method for the automated electrochemical solution‐phase synthesis of oligosaccharides. We demonstrated that electrochemical glycosylation is useful not only for intermolecular glycosylation but also for intramolecular glycosylation to synthesize cyclic oligosaccharides.

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Total synthesis of TMG-chitotriomycin based on an automated electrochemical assembly of a disaccharide building block

Cited by 33 publications

References 30 publications

Electrochemical Assembly for Synthesis of Middle‐Sized Organic Molecules

Electrochemical Assembly for Synthesis of Middle‐Sized Organic Molecules

Current Tools for Chemical Glycosylation: Where Are We Now?

Electrochemical Glycosylation as an Enabling Tool for the Stereoselective Synthesis of Cyclic Oligosaccharides

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