Direct Glycosylation of Unprotected and Unactivated Carbohydrates under Mild Conditions

Pfaffe, Matthias; Mahrwald, Rainer

doi:10.1021/ol203329u

Cited by 38 publications

(18 citation statements)

References 47 publications

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“…In an attempt to find a suitable robust donor capable of being activated in its unprotected state, Roy and Mukhopadhyay performed Fischer‐type glycosylation to establish the use of H 2 SO 4 –silica to couple unprotected free sugars with different alcohols . Interestingly, Pfaffe and Mahrwald showed that, when variously functionalized alcohols were reacted with free d ‐ribose 175 catalyzed by 10 mol % of titanium‐(IV) tert ‐butoxide and 50 mol % d ‐mandelic acid at room temperature, only coupled ribose furanosides (Scheme ) were obtained …”

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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“…252 Bypassing many of the previously examined challenges in carbohydrate chemistry, including multistep protection sequences and selective activation requirements, this glycosylation protocol presents a unique approach to the activation of the anomeric center using titanium(IV) alkoxides and α-hydroxy acids (Scheme 31). …”

Section: 1- Hydroxy Sugar Donorsmentioning

confidence: 99%

Recent Advances in Transition Metal-Catalyzed Glycosylation

2012

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Having access to mild and operationally simple techniques for attaining carbohydrate targets will be necessary to facilitate advancement in biological, medicinal, and pharmacological research. Even with the abundance of elegant reports for generating glycosidic linkages, stereoselective construction of α- and β-oligosaccharides and glycoconjugates is by no means trivial. In an era where expanded awareness of the impact we are having on the environment drives the state-of-the-art, synthetic chemists are tasked with developing cleaner and more efficient reactions for achieving their transformations. This movement imparts the value that prevention of waste is always superior to its treatment or cleanup. This review will highlight recent advancement in this regard by examining strategies that employ transition metal catalysis in the synthesis of oligosaccharides and glycoconjugates. These methods are mild and effective for constructing glycosidic bonds with reduced levels of waste through utilization of sub-stoichiometric amounts of transition metals to promote the glycosylation.

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“…The most obvious improvement is to await a method that provides furanosyl glycosides in preference to pyranosides when furanose donors are employed, thus obviating the need for any protecting groups. We also credit the outstanding efforts of the Mahrwald group for being able to develop a catalytic methodology for the synthesis of aliphatic or benzylic glycosides under neutral conditions [117–118]. We are looking forward to seeing if any expansion of the substrate scope to more complex acceptors is possible and forthcoming.…”

Section: Resultsmentioning

confidence: 98%

“…13 [117]. The yields ranged from very moderate to nearly quantitative and the reaction was reasonably stereoselective for the 1,2- trans product.…”

Section: Reviewmentioning

confidence: 99%

Strategies toward protecting group-free glycosylation through selective activation of the anomeric center

Downey

Hocek

2017

Beilstein J. Org. Chem.

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Glycosylation is an immensely important biological process and one that is highly controlled and very efficient in nature. However, in a chemical laboratory the process is much more challenging and usually requires the extensive use of protecting groups to squelch reactivity at undesired reactive moieties. Nonetheless, by taking advantage of the differential reactivity of the anomeric center, a selective activation at this position is possible. As a result, protecting group-free strategies to effect glycosylations are available thanks to the tremendous efforts of many research groups. In this review, we showcase the methods available for the selective activation of the anomeric center on the glycosyl donor and the mechanisms by which the glycosylation reactions take place to illustrate the power these techniques.

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Direct Glycosylation of Unprotected and Unactivated Carbohydrates under Mild Conditions

Cited by 38 publications

References 47 publications

Chemical O‐Glycosylations: An Overview

Chemical O‐Glycosylations: An Overview

Recent Advances in Transition Metal-Catalyzed Glycosylation

Strategies toward protecting group-free glycosylation through selective activation of the anomeric center

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