Propargyl/methyl furanosides as potential glycosyl donors

Vidadala, Srinivasa Rao; Gayatri, G.; Sastry, G. Narahari; Hotha, Srinivas

doi:10.1039/c1cc13134f

Cited by 28 publications

(28 citation statements)

References 40 publications

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“…The use of other aglycons gave similar results with respect to yields and stereoselectivity. Selective activation 10 Armed/disarmed strategy plays a very important role in the synthesis of oligosaccharides, which takes advantage of differential reactivity of C-2 protecting groups such as alkoxyls and acyloxyls. Hotha et al studied armed/disarmed effects of propargyl glycosides in the presence of a catalytic amount of AuBr 3 in the hope of realizing sequential glycosylation.…”

Section: Gold(iii)-catalyzed Glycosidation With Propargyl Glycoside Dmentioning

confidence: 99%

Chapter 8. Recent advances in gold-catalyzed glycosylation

Luo¹,

Wan²

2014

Carbohydrate Chemistry

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Section: Gold(iii)-catalyzed Glycosidation With Propargyl Glycoside Dmentioning

confidence: 99%

Chapter 8. Recent advances in gold-catalyzed glycosylation

Luo¹,

Wan²

2014

Carbohydrate Chemistry

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“…Interestingly, gold catalyst AuBr 3 alone led to a very slow reaction where propargyl furanosides were used as the donor, and the disaccharides were also formed in a low yield. Addition of AgOTf along with AuBr 3 , in turn, improved the reaction considerably, making it more spontaneous and high yielding. Benzylated propargyl furanoside 113 , acting as the armed donor, was also coupled with benzoylated propargyl pyranoside 114 (Scheme ) to give product 115 in line with the ‘armed–disarmed’ concept.…”

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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“…177 As such, the AuBr 3 catalyst activates the interglycosidic oxygen of 185 , resulting in formation of oxocarbenium 188 and simultaneous expulsion of propargyl intermediate 189 . Nucleophilic addition of the disarmed acceptor 183 to oxocarbenium 188 results in transglycoside 184 .…”

Section: Donors With Stable Methyl and Propargyl Latent Leaving Grmentioning

confidence: 99%

“…This Au(III)-mediated activation strategy has been applied to propargyl furanoside donors as well. 177 …”

Section: Donors With Stable Methyl and Propargyl Latent Leaving Grmentioning

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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Propargyl/methyl furanosides as potential glycosyl donors

Cited by 28 publications

References 40 publications

Chapter 8. Recent advances in gold-catalyzed glycosylation

Chapter 8. Recent advances in gold-catalyzed glycosylation

Chemical O‐Glycosylations: An Overview

Recent Advances in Transition Metal-Catalyzed Glycosylation

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