Naturally Occurring C-Glycosyl Compounds

Haynes, L. J.

doi:10.1016/s0096-5332(08)60244-1

Cited by 26 publications

(7 citation statements)

References 48 publications

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“…For more than 50 years, C -glycosides have been identified in plants [ 33 – 34 ] as secondary metabolites. At least 5 families of aromatic aglycones have been reported to be C -glycosylated: flavones, xanthones, chromones, anthrones, and gallic acids.…”

Section: Reviewmentioning

confidence: 99%

Enzymatic synthesis of glycosides: from natural O- and N-glycosides to rare C- and S-glycosides

Ati

Lafite

Daniellou

2017

Beilstein J. Org. Chem.

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Carbohydrate related enzymes, like glycosyltransferases and glycoside hydrolases, are nowadays more easily accessible and are thought to represent powerful and greener alternatives to conventional chemical glycosylation procedures. The knowledge of their corresponding mechanisms has already allowed the development of efficient biocatalysed syntheses of complex O-glycosides. These enzymes can also now be applied to the formation of rare or unnatural glycosidic linkages.

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Section: Reviewmentioning

confidence: 99%

Enzymatic synthesis of glycosides: from natural O- and N-glycosides to rare C- and S-glycosides

Ati

Lafite

Daniellou

2017

Beilstein J. Org. Chem.

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“…Numerous biologically important aryl C -glycosides have been isolated and identified . The development of efficient and stereocontrolled C -glycosylations has been an area of interest for many years .…”

Section: C-glycosidesmentioning

confidence: 99%

Stereocontrolled Glycosyl Transfer Reactions with Unprotected Glycosyl Donors

Hanessian

Lou²

2000

Chem. Rev.

165

103

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I. Introduction 4443 II. Challenges of Glycoside Synthesis 4444 III. Brief Survey of Post-1980 Methods of Anomeric Activation 4444 1. Non-Bromide, -Chloride, -Iodide Methods for Anomeric Activation 4444 2. New Generations of Anomeric Leaving Groups and Activation Methods 4445 IV. Glycosylation with Unprotected Glycosyl Donors 4446 1. O-Glycosides 4446 A. Fischer-type Glycosylation of Alcohols 4446 B. Miscellaneous Methods 4447 2. Glycosylamines and Glycosyl Azides 4447 3. C-Glycosides 4448 V. Remote Activation Concept 4448 VI. Stereocontrolled Glycosylation Using 3-Methoxypyridyl (MOP) O-Unprotected Glycosyl Donors 4449 1. Design, Concept, and Activation Mechanism 4449 2. Preparation of MOP Glycosyl Donors 4451 3. Glycosylation with O-Unprotected MOP Glycosyl Donors 4452 A. Synthesis of O-Glycosides and Oligosaccharides 4452 B. Selective Activation 4453 C. Stereocontrolled Synthesis of Glycosyl 1-Carboxylates and Glycosyl Azides 4456 D. Stereocontrolled Synthesis of Glycosyl 1-Phosphates and Glycosyl Nucleotides 4457 4. Solid-Phase Synthesis Using MOP Donors and Acceptors 4458 A. Linking Strategy 4458 B. Synthesis of O-Glycosides and Oligosaccharides on Solid Support 4459 VII. Conclusion 4460 VIII. Acknowledgments 4461 IX. References 4461

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“…Analytical progress in this field was very rapid, the results of which were reviewed by HAYNES (1963 and. The anthracene derivatives form an important class which are found as a wide variety of C-glycosidic compounds in species of Aloe and Rhamnus (HAYNES 1965, GIBBS 1974. Another class, the C-glycosyl flavones, are widespread in the plant kingdom (ALSTON 1968, GIBBS 1974.…”

Section: C-glycosidesmentioning

confidence: 99%

Glycosylation of Heterosides (Glycosides)

Franz¹

1982

Plant Carbohydrates I

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Naturally Occurring C-Glycosyl Compounds

Cited by 26 publications

References 48 publications

Enzymatic synthesis of glycosides: from natural O- and N-glycosides to rare C- and S-glycosides

Enzymatic synthesis of glycosides: from natural O- and N-glycosides to rare C- and S-glycosides

Stereocontrolled Glycosyl Transfer Reactions with Unprotected Glycosyl Donors

Glycosylation of Heterosides (Glycosides)

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