Organocatalysis: A recent development on stereoselective synthesis of o-glycosides

Yadav, Ram Naresh; Hossain, Md. Firoj; Das, Aparna; Srivastava, Ashok; Banik, Bimal K.

doi:10.1080/01614940.2022.2041303

Cited by 14 publications

(5 citation statements)

References 157 publications

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“…Saccharides are structurally very challenging compounds with respect to reliable and repeatable determination [37,41,42,63,66,67,82,83]. But, a few notes about their analyses are found: First, it is advantageous to detect the whole original compound or large saccharide compounds which are cleavages of specific pieces.…”

Section: Recent Views About Liquid Chromatographic Methods In Sacchar...mentioning

confidence: 99%

“…The DP and structural acetylation of ChOSs are identified by β−1,4-linked glucosamines. However, free N-acetyl glucosamines are used only for the identification and mapping of human N-and O-linked glycoproteomes (N-linked glycan, O,Nacetylated glucosamine, and O,N-acetyl galactosamine) [66][67][68]. In nature, oligosaccharides and glycan-binding proteins react with amino groups by covalent bonds, but in glycolipids, the glycose bonds are randomly formed with hydroxyl, carboxyl, and amide groups [69][70][71].…”

Section: Homologous and Heterogeneous Oligo-and Polysaccharides And G...mentioning

confidence: 99%

“…[156,174,177,[262][263][264][265]. MS allowed the identification of O-and C-glycosides and diglycosides from plants [67,143,158]. Anomeric forms of monosaccharides, glycosides, and aglycones are studied with nESI-MS which permits a wide and outstanding possibility for collecting accurate structural information, especially when MS/MS and Orbitrap-MS are used.…”

Section: Ms Of Macro-scale Saccharidesmentioning

confidence: 99%

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Research of saccharides and related biocomplexes: A review with recent techniques and applications

Sirén

2024

J of Separation Science

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Saccharides and biocompounds as saccharide (sugar) complexes have various roles and biological functions in living organisms due to modifications via nucleophilic substitution, polymerization, and complex formation reactions. Mostly, mono‐, di‐, oligo‐, and polysaccharides are stabilized to inactive glycosides, which are formed in metabolic pathways. Natural saccharides are important in food and environmental monitoring. Glycosides with various functionalities are significant in clinical and medical research. Saccharides are often studied with the chromatographic methods of hydrophilic interaction liquid chromatography and anion exchange chromatograpy, but also with capillary electrophoresis and mass spectrometry with their on‐line coupling systems. Sample preparation is important in the identification of saccharide compounds. The cases discussed here focus on bioscience, clinical, and food applications.

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Section: Recent Views About Liquid Chromatographic Methods In Sacchar...mentioning

confidence: 99%

Section: Homologous and Heterogeneous Oligo-and Polysaccharides And G...mentioning

confidence: 99%

Section: Ms Of Macro-scale Saccharidesmentioning

confidence: 99%

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Research of saccharides and related biocomplexes: A review with recent techniques and applications

Sirén

2024

J of Separation Science

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“…For glycosylation, glycosyl donors such as thioglycosides are often utilised in the presence of promoters such as methyl triflate, N -iodosuccinimide-triflic acid, and iodonium dicollidine perchlorate. 47a…”

Section: Application In Carbohydratesmentioning

confidence: 99%

Application of N-Bromosuccinimide in Carbohydrate Chemistry

Bera,

Mondal,

Chatterjee

2023

SynOpen

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This article describes the use of N-bromosuccinimide in different organic group transformations in carbohydrate chemistry. A comprehensive discussion on the synthesis of deoxysugars through selective O-benzylidene fragmentation, photobromination, halogenation, oxidation, and polymerisation of different carbohydrate moieties with the aid of N-bromosuccinimide (NBS) is presented. The use of NBS in the most significant glycosylation methods and in oligosaccharide synthesis is also discussed.

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“…Most glycosylation reactions involve some promoter to activate the leaving group, causing the formation of the oxocarbenium ion and the nucleophilic attack. The challenge in the search for activators that favor stereocontrol in the anomeric center is not trivial because of the need for chemical species that interact with the glycosyl donor to occur exclusively in the glycosidic bond from the underside face by the direct participation of the promoter to the exo-anomeric effect [56][57][58]. There is a strong emphasis on metals as promoters due to the availability of frontier orbitals, enabling new bonds as Lewis Acids [59].…”

Section: Promotermentioning

confidence: 99%

Recent Advances Related to Anomeric and Exo-anomeric Effects in Carbohydrate Chemistry

Filho,

Freitas,

Neto

et al. 2023

IRJPAC

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The anomeric effect in carbohydrate chemistry is known as the interaction between the OHd substituent at the anomeric position to favor an axial orientation rather than an equatorial one, despite the increased 1,3-diaxial interactions. In the anomeric effect, a sugar ring is stabilized by an electronegative substituent at the C1 carbon, also known as the anomeric carbon. The stabilization is thought to result from interactions between lone electron pairs on oxygen and a C1 antibonding orbital. On the other hand, the anomeric effect can be of two types: endo-anomeric and exo-anomeric. The effect is called endo-anomeric when the lone pair comes from the oxygen atom in the sugar ring and exo-anomeric when the lone pair comes from oxygen in a substituent on C1. Several factors influence the anomeric effect. In this way, this review aims to describe the recent advances in main theories, observations, and advances achieved in the last decades related to the anomeric effect. GRAPHICAL ABSTRACT

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Organocatalysis: A recent development on stereoselective synthesis of o-glycosides

Cited by 14 publications

References 157 publications

Research of saccharides and related biocomplexes: A review with recent techniques and applications

Research of saccharides and related biocomplexes: A review with recent techniques and applications

Application of N-Bromosuccinimide in Carbohydrate Chemistry

Recent Advances Related to Anomeric and Exo-anomeric Effects in Carbohydrate Chemistry

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