Solid-Phase Oligosaccharide Synthesis:  Preparation of Complex Structures Using a Novel Linker and Different Glycosylating Agents

Andrade, Rodrigo; Plante, Obadiah J.; Melean, Luis G.; Seeberger, Peter H.

doi:10.1021/ol991071+

Cited by 119 publications

(111 citation statements)

References 38 publications

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“…[276] Enormous progress has been made with trichloroacetimidate-based SPOS. One important advance was the successful preparation of Oglycosyl trichloroacetimidates with an O-Fmoc protecting group and the demonstration of their suitability for oligosaccharide synthesis on a solid support.…”

Section: Solid-phase Oligosaccharide Synthesismentioning

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: Solid-phase Oligosaccharide Synthesismentioning

confidence: 99%

New Principles for Glycoside‐Bond Formation

2009

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“…[126] The same group has also investigated the concept of resin capture, that is, attachment of the resin to the product of a ROM-CM reaction. [82] Seeberger and co-workers [127,128] developed a novel octenediol-based linker, which is cleaved by CM with ethylene gas promoted by 6.…”

Section: Reactions On a Solid Supportmentioning

confidence: 99%

Recent Developments in Olefin Cross‐Metathesis

2003

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Among the many types of transition-metal-catalyzed C-C bond-forming reactions, olefin metathesis has come to the fore in recent years owing to the wide range of transformations that are possible with commercially available and easily handled catalysts. Consequently, olefin metathesis is now widely considered as one of the most powerful synthetic tools in organic chemistry. Until recently the intermolecular variant of this reaction, cross-metathesis, had been neglected despite its potential. With the evolution of new catalysts, the selectivity, efficiency, and functional-group compatibility of this reaction have improved to a level that was unimaginable just a few years ago. These advances, together with a better understanding of the mechanism and catalyst-substrate interactions, have brought us to a stage where more and more researchers are employing cross-metathesis reactions in multistep procedures and in the synthesis of natural products. The recent inclusion of alkynes and hindered bicyclic olefins as viable substrates for bimolecular metathesis coupling, the discovery of enantioselective cross-metathesis and cross-metathesis in water, and the successful marriage of metathesis and solid-phase organic synthesis has further widened the scope of this versatile reaction.

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“…A small library of 12 trisaccharides was synthesized using a split-mix approach to generate anomeric mixtures. with a versatile octenediol linker can be successfully accomplished [23]. Other solid-phase approaches described in the literature include the glycal assembly method for the synthesis of polymer bound thioethyl glycosyl donors for the synthesis of β-linked oligosaccharides [24]; the synthesis of thio-oligosaccharides by nucleophilic substitution of triflate activated glycosides by resin-bound sugar-1-thiolate containing unprotected hydroxyl groups [25], and the use of a novel photocleavable aglycon linker for the synthesis of a dodecasaccharide with high sterospecificity [26].…”

Section: Methodsmentioning

confidence: 99%

High-throughput Chemistry toward Complex Carbohydrates and Carbohydrate-like Compounds a

Randell

Barkley²,

Arya³

2002

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Solid-Phase Oligosaccharide Synthesis: Preparation of Complex Structures Using a Novel Linker and Different Glycosylating Agents

Abstract: [formula: see text] A beta-(1-->4)-linked trisaccharide was prepared in 53% yield on a polymer support using glycosyl phosphates and released by cross-metathesis of a novel linker to reveal the anomeric n-pentenyl glycoside. Heptasaccharide 33 was prepared in 9% yield in 14 steps.

Cited by 119 publications

References 38 publications

New Principles for Glycoside‐Bond Formation

New Principles for Glycoside‐Bond Formation

Recent Developments in Olefin Cross‐Metathesis

High-throughput Chemistry toward Complex Carbohydrates and Carbohydrate-like Compounds a

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