Chapter 8. Recent advances in gold-catalyzed glycosylation

Luo, Jun; Wan, Qian

doi:10.1039/9781849739986-00140

Cited by 16 publications

(7 citation statements)

References 34 publications

(45 reference statements)

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“…On the other hand, the conversion of hemiacetal 7 into shelf‐stable alkynylbenzoate donor 15 was highly efficient upon treatment with o ‐hexynylbenzoic acid ( 14 ) and EDCI in the presence of DIPEA and DMAP. [ 54‐61 ] Similar results were obtained in the transformation of hemiacetal 12 into the corresponding trichloroacetimidate 16 and alkynylbenzoate 17 .…”

Section: Resultssupporting

confidence: 62%

Synthesis and Antiproliferative Activities of OSW‐1 Analogues Bearing 2”‐O‐p‐Acylaminobenzoyl Residues^†

et al. 2020

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Section: Resultssupporting

confidence: 62%

Synthesis and Antiproliferative Activities of OSW‐1 Analogues Bearing 2”‐O‐p‐Acylaminobenzoyl Residues^†

et al. 2020

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“…Glycosylation, the formation of a new glycosidic bond between two sugar units, has remained the central reaction in carbohydrate synthesis. Since the first report on glycoside synthesis by Michael in 1879 and Fischer glycosylation in 1893, followed by the advent of the Koenigs–Knorr reaction in 1901, glycosylation has undergone many changes over the years. ,− Glycosylation is probably the most intriguing reaction that has mesmerized the carbohydrate community for such a long time. In contrast to the synthesis of other biomolecules such as proteins and nucleic acids, wherein no regio or stereochemical issues are involved in the coupling step, sugar coupling has to be controlled such that only one of several reactive hydroxyl groups is coupled with the other partner and with the desired stereoselectivity (α or β).…”

Section: Glycosylationmentioning

confidence: 99%

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

et al. 2018

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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.

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“…The use of glycosyl ortho-alkynylbenzoates for natural glycoside synthesis and the use of gold catalyst for glycosylations in general have recently been reviewed …”

Section: Alkyne-based Glycosyl Donorsmentioning

confidence: 99%

Catalytic Glycosylations in Oligosaccharide Synthesis

2018

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Catalytic glycosylation has been a central reaction in carbohydrate chemistry since its introduction by Fischer 125 years ago, but it is only in the past three to four decades that catalytic methods for synthesizing oligosaccharides have appeared. Despite the development of numerous elegant and ingenious catalytic glycosylation methods, only a few are in general use. This review covers all methods of catalytic glycosylation with the focus on the development and application in oligosaccharide synthesis and provide an overview of the scope and limitations of these. The review also includes relevant mechanistic studies of catalytic glycosylations. The future of catalytic glycosylation chemistry is discussed, including specific, upcoming methods and possible directions for the field of research in general.

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Chapter 8. Recent advances in gold-catalyzed glycosylation

Cited by 16 publications

References 34 publications

Synthesis and Antiproliferative Activities of OSW‐1 Analogues Bearing 2”‐O‐p‐Acylaminobenzoyl Residues^†

Synthesis and Antiproliferative Activities of OSW‐1 Analogues Bearing 2”‐O‐p‐Acylaminobenzoyl Residues^†

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

Catalytic Glycosylations in Oligosaccharide Synthesis

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Chapter 8. Recent advances in gold-catalyzed glycosylation

Cited by 16 publications

References 34 publications

Synthesis and Antiproliferative Activities of OSW‐1 Analogues Bearing 2”‐O‐p‐Acylaminobenzoyl Residues†

Synthesis and Antiproliferative Activities of OSW‐1 Analogues Bearing 2”‐O‐p‐Acylaminobenzoyl Residues†

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

Catalytic Glycosylations in Oligosaccharide Synthesis

Contact Info

Product

Resources

About

Synthesis and Antiproliferative Activities of OSW‐1 Analogues Bearing 2”‐O‐p‐Acylaminobenzoyl Residues^†

Synthesis and Antiproliferative Activities of OSW‐1 Analogues Bearing 2”‐O‐p‐Acylaminobenzoyl Residues^†