Recent trends in the synthesis of O-glycosides of 2-amino-2-deoxysugars

Bongat, Aileen F. G.; Demchenko, Alexei V.

doi:10.1016/j.carres.2006.10.021

Cited by 199 publications

(121 citation statements)

References 487 publications

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“…A comprehensive review published recently on the synthesis of 2-aminoglycosides provides more information on these protecting groups. [222] The dimethylmaleoyl (DMM) group has attracted much attention as an N-protecting group owing to its excellent properties. [223] In contrast to the phthaloyl group, it can be removed readily with a base and subsequent treatment with an acid.…”

Section: Neighboring Protecting Groups That Lead To 12-trans Glycosidesmentioning

confidence: 99%

New Principles for Glycoside‐Bond Formation

2009

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Increased understanding of the important roles that oligosaccharides and glycoconjugates play in biological processes has led to a demand for significant amounts of these materials for biological, medicinal, and pharmacological studies. Therefore, tremendous effort has been made to develop new procedures for the synthesis of glycosides, whereby the main focus is often the formation of the glycosidic bonds. Accordingly, quite a few review articles have been published over the past few years on glycoside synthesis; however, most are confined to either a specific type of glycoside or a specific strategy for glycoside synthesis. In this Review, new principles for the formation of glycoside bonds are discussed. Developments, mainly in the last ten years, that have led to significant advances in oligosaccharide and glycoconjugate synthesis have been compiled and are evaluated.

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Section: Neighboring Protecting Groups That Lead To 12-trans Glycosidesmentioning

confidence: 99%

New Principles for Glycoside‐Bond Formation

2009

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“…The biological significance of b-1,4-linked oligomers of glucosamine (e.g., chitin) is well recognized [3,52]. Also, the hydroxyl group at the C-4 position of GlcN is known to be relatively unreactive [3,[52][53][54].…”

Section: Usefulness Of "Active-latent" Strategy Toward Oligosaccharidesmentioning

confidence: 99%

“Active–Latent” Thioglycosyl Donors and Acceptors in Oligosaccharide Syntheses

Shiao

Roy

2010

Reactivity Tuning in Oligosaccharide Assembly

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The fine tuning of thioglycosides used as glycosyl donors occurs through careful manipulations of the aglycon's nucleofugality, for example, by using "active-latent" principles. In the first section, the control of the relative leaving group abilities will be discussed in terms of electronic factors, including electron-donating/withdrawing substituents. In the second section, the nucleofugality will be adjusted by steric factors. Quantitative reactivity relationships will then be documented followed by presentation of other controlling elements including locked conformations, solvents, and promoters that will be illustrated throughout.

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“…The most important classes of oligoconjugates and naturally occurring oligosaccharides contain 2-amino-2-deoxysugar moieties, which are connected to other residues, commonly via a 1,2-trans-glycosidic linkage. 2 Specifically, 2-N-acetamido-2-deoxyglycosides, most frequently of D-glucose and D-galactose sequences, are found abundantly as glycoconjugates in living organisms. These 2-N-acetamido-2-deoxyglycosides contain glucosamine units which can be glycosylated through O-3, O-4, and O-6 positions.…”

Section: Introductionmentioning

confidence: 99%

“…Owing to the increasing interest in 2-amino-sugar oligosaccharides, special efforts have been dedicated to searches for efficient synthetic approaches to such complex molecules involving efficient, simple, region-and stereo-selective methods. 2 To date, one of the most efficient strategies to prepare oligosaccharides consists in the preparation of key building blocks of di-, tri-, and higher-oligosaccharides, that can be further used to assemble larger molecules.…”

Section: Introductionmentioning

confidence: 99%