Photo-induced glycosylation using reusable organophotoacids

Iwata, Ryosuke; Uda, Kanjiro; Takahashi, Daisuke; Toshima, Kazunobu

doi:10.1039/c4cc04753b

Cited by 47 publications

(31 citation statements)

References 15 publications

(6 reference statements)

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“…Photoinduced reactions have attracted much interest in the last few years. Organic photoacids have been implemented for the activation of trichloroacetimidates under photoirradiation . An organic photoacid excited upon photoirradiation subsequently activates glycosyl imidates and facilitates coupling with corresponding alcohols as acceptors.…”

Section: Glycosylationsmentioning

confidence: 99%

Chemical O‐Glycosylations: An Overview

2016

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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.

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Section: Glycosylationsmentioning

confidence: 99%

Chemical O‐Glycosylations: An Overview

2016

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“…These examples demonstrate that the catalytic system is tolerant of common alcohol (acetal, ether, ester) and amine (carbamate) protecting groups (3)(4)(5)(6)(7)(8)(9)(10)(11). Moreover,t he glycosylation of N-Bocprotected serine,c holesterol, and ap rotected nucleotide proceeded smoothly to give the corresponding products (11)(12)(13)iny ields of 74, 91, and 80 %, respectively. Moreover,t he glycosylation of N-Bocprotected serine,c holesterol, and ap rotected nucleotide proceeded smoothly to give the corresponding products (11)(12)(13)iny ields of 74, 91, and 80 %, respectively.…”

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confidence: 87%

“…[6] Whereas several direct approaches have been developed, [7] they rely on stoichiometric amounts of promoters or synthetic precursors that need to be prepared in several steps.The direct addition of an alcohol to an activated glycal in acatalyzed process remains the most atom-efficient route to 2-deoxyglycosides. [9] Similar photoacids have been utilized in polymer synthesis, [10] proton-transfer processes, [9c,11] acid-catalyzed reactions, [12] molecular switching, [13] and photodynamic therapy. [9] Similar photoacids have been utilized in polymer synthesis, [10] proton-transfer processes, [9c,11] acid-catalyzed reactions, [12] molecular switching, [13] and photodynamic therapy.…”

mentioning

confidence: 99%

Stereoselective Synthesis of 2‐Deoxyglycosides from Glycals by Visible‐Light‐Induced Photoacid Catalysis

Zhao

Wang

2018

Angewandte Chemie

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The direct, photoacid-catalyzed synthesis of 2-deoxyglycosides from glycals is reported. As eries of phenol-conjugated acridinium-based organic photoacids were rationally designed, synthesized, and studied alongside the commercially available phenolic catalyst eosin Y. In the presence of such ap hotoacid catalyst and light, synthetic glycals were activated and coupled with arange of alcohols to afford2 -deoxyglycosides in good yields and with excellent a-selectivity.

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“…Toshima et al had previously shown that a naphthol‐derived organophotoacid activator could be employed to promote the coupling between a glycosyl trichloroacetimidate and several alcohol nucleophiles, under photoirradiation. The reaction proceeded smoothly to give the corresponding glycosides in high yields with varying degrees of stereocontrol, which was substrate dependent . In an effort to find an organoacid that could help control the α/β‐selectivity of the redox‐type photoinduced glycosylation reaction, aryl thioureas were subsequently evaluated under long wavelength UV irradiation .…”

Section: Thiourea Catalyzed Glycosylationsmentioning

confidence: 99%

Recent Advances in Organocatalytic Glycosylations

Williams

Galan

2017

Eur J Org Chem

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General rightsThis document is made available in accordance with publisher policies. Please cite only the published version using the reference above. Full terms of use are available: http://www.bristol.ac.uk/pure/about/ebr-terms MICROREVIEW Recent Advances in Organocatalytic GlycosylationsRyan Williams [a] and M. Carmen Galan* [a] Dedication ((optional))Abstract: Carbohydrates play a pivotal role in biological systems and present an opportunity to develop potent carbohydrate derived therapeutics and diagnostic tools for the treatment and detection of disease. To better comprehend the biological functions of carbohydrates, access to pure and structurally defined oligosaccharides is needed. Oligosaccharides are commonly synthesized by chemical means, however, despite progress in glycosylation chemistry, the efficient and stereoselective formation of glycosidic bonds by mild, non-toxic and low-cost methods remains a challenge. Organocatalysis is an exciting field that utilizes small organic molecules to effect chemical transformation where traditionally transition metal catalysis would be required. This microreview presents recent advances in the application of organocatalysis to carbohydrate chemistry and in particular to the stereoselective synthesis of oligosaccharides.

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Photo-induced glycosylation using reusable organophotoacids

Cited by 47 publications

References 15 publications

Chemical O‐Glycosylations: An Overview

Chemical O‐Glycosylations: An Overview

Stereoselective Synthesis of 2‐Deoxyglycosides from Glycals by Visible‐Light‐Induced Photoacid Catalysis

Recent Advances in Organocatalytic Glycosylations

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