Pentavalent Bismuth as a Universal Promoter for S-Containing Glycosyl Donors with a Thiol Additive

Kabotso, Daniel E. K.; Pohl, Nicola L. B.

doi:10.1021/acs.orglett.7b02080

Cited by 15 publications

(7 citation statements)

References 41 publications

(56 reference statements)

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“…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

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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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Section: Glycosylationmentioning

confidence: 99%

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

et al. 2018

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“…The best-known examples of these leaving groups include trichloroacetimidoyl (TCAI), , N -phenyl trifluoroacetimidoyl (PTFAI), and phosphites/phosphates . The use of transition metal catalysts based on palladium , and nickel , developed by Nguyen et al for TCAI donors offers new opportunities for stereocontrol . Many other current methodologies for glycosylation, such as glycosylation with S-aryl/alkyl thioglycosides, use stoichiometric promoters.…”

Section: Traditional Manual Synthesis Of Oligosaccharidesmentioning

confidence: 99%

“…Many other current methodologies for glycosylation, such as glycosylation with S-aryl/alkyl thioglycosides, use stoichiometric promoters. Bi(V) , and Au(III) catalyzed activations of thioglycosides represent other new promising directions in glycosylation chemistry. , Recently there has been an explosion in the study of gold-catalyzed activation of alkynes to exploit the low oxophilic character of gold and the excellent functional group compatibilities these catalysts exhibit. ,,− …”

Section: Traditional Manual Synthesis Of Oligosaccharidesmentioning

confidence: 99%

Automated Chemical Oligosaccharide Synthesis: Novel Approach to Traditional Challenges

et al. 2018

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Advances in carbohydrate chemistry have certainly made common oligosaccharides much more accessible. However, many current methods still rely heavily upon specialized knowledge of carbohydrate chemistry. The application of automated technologies to chemical and life science applications such as genomics and proteomics represents a vibrant field. These automated technologies also present opportunities for their application to organic synthesis, including that of the synthesis of oligosaccharides. However, application of automated methods to the synthesis of carbohydrates is an underdeveloped area as compared to other classes of biomolecules. The overarching goal of this review article is to present the advances that have been made at the interface of carbohydrate chemistry and automated technology.

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“…The catalytic cycle is not further discussed in the mechanistic paper and not clear from the mechanic proposal and hence remains somewhat unclear whether the Ph 3 Bi(OTf) 2 or another species formed from it remains intact or is generated under the reaction conditions. Later work using this promoter was done with an excess …”

Section: Thioglycosidesmentioning

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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Pentavalent Bismuth as a Universal Promoter for S-Containing Glycosyl Donors with a Thiol Additive

Cited by 15 publications

References 41 publications

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

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

Automated Chemical Oligosaccharide Synthesis: Novel Approach to Traditional Challenges

Catalytic Glycosylations in Oligosaccharide Synthesis

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