Intramolecular Glycosidation Reactions

Madsen, Jacob; Bols, Mikael; Ernst, Beat; Hart, Gerald W.; Sînaÿ, Pierre

doi:10.1002/9783527618255.ch18

Cited by 7 publications

(3 citation statements)

References 41 publications

(18 reference statements)

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“…An area of intramolecular glycosylation has also been developed to enhance the production of difficult glycosidic linkages. A better stereocontrol is achieved by tethering the reaction counterparts and restricting the glycosyl acceptor attack. − The best known example, intramolecular aglycone delivery (IAD), was introduced by Barresi and Hindsgaul . Over the years, IAD has evolved into a powerful means to perform glycosylations of complex targets with high efficiency and yields. − The major improvement of this approach has emerged with the implementation of a 2-naphthylmethyl group (Nap) as a tether group .…”

Section: Traditional Manual Synthesis Of Oligosaccharidesmentioning

confidence: 99%

Automated Chemical Oligosaccharide Synthesis: Novel Approach to Traditional Challenges

et al. 2018

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Advances in carbohydrate chemistry have certainly made common oligosaccharides much more accessible. However, many current methods still rely heavily upon specialized knowledge of carbohydrate chemistry. The application of automated technologies to chemical and life science applications such as genomics and proteomics represents a vibrant field. These automated technologies also present opportunities for their application to organic synthesis, including that of the synthesis of oligosaccharides. However, application of automated methods to the synthesis of carbohydrates is an underdeveloped area as compared to other classes of biomolecules. The overarching goal of this review article is to present the advances that have been made at the interface of carbohydrate chemistry and automated technology.

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Section: Traditional Manual Synthesis Of Oligosaccharidesmentioning

confidence: 99%

Automated Chemical Oligosaccharide Synthesis: Novel Approach to Traditional Challenges

et al. 2018

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“…An issue of controlling the stereoselectivity of glycosylations has been approached in a variety of modes. , Among these, intramolecular approaches occupy an important niche among other methods available. − The basis of the concept is that the two glycosylation components, glycosyl donor and acceptor, are tethered together using a suitable linker. The purpose of this tethering is to achieve an efficient facial selectivity due to steric or geometric constraints and forces.…”

Section: Introductionmentioning

confidence: 99%

Templated Oligosaccharide Synthesis: Driving Forces and Mechanistic Aspects

2016

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We previously communicated that high α-selectivity that can be achieved in intramolecular glycosylations using a rigid bisphenol A template supplemented with linkers of various lengths. Herein, we present our investigation of the mechanistic aspects of the templated synthesis that helped to design an improved template-linker combination. We demonstrate that bisphenol A as the template in combination with phthaloyl linker allows for superior stereoselectivity and yields in glycosylations. Several mechanistic studies explore origins of the enhanced stereoselectivity and yields achieved using the phthaloyl linker.

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“…The issue of controlling the stereoselectivity of glycosylations has been approached in a variety of modes. , For instance, intramolecular approaches occupy an important niche among other methods available. Many attractive intramolecular glycosylation methods have emerged during the past two decades. − The underlying concept is that two glycosylation components, the glycosyl donor and acceptor, are tethered together using a cleavable linker. The purpose of this tethering is to achieve efficient facial selectivity due to steric or geometric constraints or forces that may help to control the stereoselectivity of the glycosylation.…”

mentioning

confidence: 99%

Templated Oligosaccharide Synthesis: The Linker Effect on the Stereoselectivity of Glycosylation

et al. 2016

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A new method for intramolecular oligosaccharide synthesis that is conceptually related to the general molecular clamp approach is introduced. Exceptional α-selectivity has been achieved in a majority of applications. Unlike other related concepts, this approach is based on the bisphenol A template, which allows one to connect multiple building blocks to perform templated oligosaccharide synthesis with complete stereoselectivity. This principle was demonstrated by the synthesis of an α,α-linked trisaccharide.

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Intramolecular Glycosidation Reactions

Cited by 7 publications

References 41 publications

Automated Chemical Oligosaccharide Synthesis: Novel Approach to Traditional Challenges

Automated Chemical Oligosaccharide Synthesis: Novel Approach to Traditional Challenges

Templated Oligosaccharide Synthesis: Driving Forces and Mechanistic Aspects

Templated Oligosaccharide Synthesis: The Linker Effect on the Stereoselectivity of Glycosylation

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