Direct Preparation of N‐Glycosidic Bond‐Linked Nonionic Carbohydrate‐Based Surfactant (NICBS) via Ritter Reaction

Wang, Zerong Daniel; Sheikh, Samia O.; Cox, Shannon; Zhang, Haoyang; Massey, Keegan

doi:10.1002/ejoc.200700079

Cited by 15 publications

(5 citation statements)

References 67 publications

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“…Am echanism was proposed by Wang et al in 2007. [98] Firstly, an oxocarbenium cation is formed in thep resence of aL ewis acid (e.g.,T MSOTf), followed by an ucleophilic attack by the nitrile. Thisi sf ollowed by hydrolysis and formation of the amide bond (Scheme 30).…”

Section: Ritter Reactionmentioning

confidence: 99%

“…In one example, d-glucose was treated with acetonitrile in the presence of AgClO 4 and TMSOTf. [98] After 24 hours at room temperature the reaction was quenched with triethylamine followed by silica gel filtration. After acetylation, the b-configured product was reported in 27 %y ield (Scheme30).…”

Section: Ritter Reactionmentioning

confidence: 99%

“…Proposed reaction mechanism for carbohydrates in the Ritter reaction. [98] The reactivity of the oxazolidinones wase xploited by Ichikawa and co-workers in 2006. [106] They demonstratedt he synthesis of ag lucoseo xazolidinone with triphenylphosphine and CO 2 in acetonei n9 7% yield, followed by its reaction with different amines in water to form urea-linkedn eo-glycoconjugates.…”

Section: Glycosylureasmentioning

confidence: 99%

“…A mechanism was proposed by Wang et al. in 2007 . Firstly, an oxocarbenium cation is formed in the presence of a Lewis acid (e.g., TMSOTf), followed by a nucleophilic attack by the nitrile.…”

Section: Glycosyl Amidesmentioning

confidence: 99%

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Chemoselective Reactions for the Synthesis of Glycoconjugates from Unprotected Carbohydrates

et al. 2017

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Glycobiology is the comprehensive biological investigation of carbohydrates. The study of the role and function of complex carbohydrates often requires the attachment of carbohydrates to surfaces, their tagging with fluorophores, or their conversion into natural or non-natural glycoconjugates, such as glycopeptides or glycolipids. Glycobiology and its "omics", glycomics, require easy and robust chemical methods for the construction of these glycoconjugates. This review gives an overview of the rapidly expanding field of chemical reactions that selectively convert unprotected carbohydrates into glycoconjugates through the anomeric position. The discussion is divided in terms of the anomeric bond type of the newly formed glycoconjugates, including O-, N-, S-, and C-glycosides.

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Section: Ritter Reactionmentioning

confidence: 99%

Section: Ritter Reactionmentioning

confidence: 99%

Section: Glycosylureasmentioning

confidence: 99%

Section: Glycosyl Amidesmentioning

confidence: 99%

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Chemoselective Reactions for the Synthesis of Glycoconjugates from Unprotected Carbohydrates

et al. 2017

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“…Amphiphilic N-alkylglucamines can be obtained from glucose by reaction with fatty amines in refluxing methanol, followed by reduction over Raney nickel under hydrogen pressure or using sodium borohydride. Glucamide surfactants can be subsequently obtained by acylation using various conditions (Figure 26) [208][209][210][211]. The formation of by-products and co-products can be avoided when using an enzymatic route [212,213].…”

Section: Reductive Aminationmentioning

confidence: 99%

Carbohydrate-Based Amphiphiles: Resource for Bio-based Surfactants

Wang¹,

Queneau²

2018

Encyclopedia of Sustainability Science and Technology

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GLOSSARY Carbohydrates are a family of biomolecules, ubiquitous in Nature, based on a common polyhydoxylated backbone though varying in size (from small molecules to macromolecules), in fine structure (configuration and functionalization), and possessing a wide range of biological properties and roles making them indispensable to life. Amphiphiles are molecular architectures with parts exhibiting different types of polarity, generally including hydrophilic and hydrophobic groups. Surfactants are molecules possessing the ability to modulate interfacial tension, notably water surface tension. Bio-based chemicals are chemical products which are obtained by transformation of a starting material arising from biomass, such as carbohydrates, fats, proteins, terpenes. DEFINITION OF THE SUBJECT Surfactants are commodity chemicals used in an incredibly wide range of situations of the everyday life, and must therefore be improved constantly in terms of environmental impact, sustainability and performance. One way towards more sustainable surfactants is the use of renewable resources as raw materials for their manufacture, in place of fossil ones. Since the structure of surfactant combines a polar part to a hydrophobic one, carbohydrates, which are very polar molecules, appear as ideal candidates for serving as renewable building blocks in the synthesis of bio-based surfactants. Developed first with the aim of providing added-value to some agricultural crops and by products, this strategy shows nowadays a rebirth in the context of green and sustainable chemistry. The chapter illustrates, from the chemical point of view, the diversity of molecular structures which belong to the family of carbohydrate-based surfactants.

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Ritter Reaction

2010

Comprehensive Organic Name Reactions and Reagents

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The strong acid‐promoted amidation of alcohol or olefin with nitrile is generally known as the Ritter reaction. It has been reported that some other types of molecules can also undergo this reaction under similar conditions by the formation of carbocations, such as trioxane, N ‐tosylazetidine, aziridine, oxirane, and epoxide. The outcome of this reaction depends on the reactivity of nitriles and the stability of carbocations. The study finds that the temperature may affect the reaction. Furthermore, it has been found that stereochemistry is completely retained in this reaction when a bromo group is present at the neighboring position. Various modifications of the original protocol of this reaction have been discussed. This reaction has very wide applications in organic synthesis.

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Direct Preparation of N‐Glycosidic Bond‐Linked Nonionic Carbohydrate‐Based Surfactant (NICBS) via Ritter Reaction

Cited by 15 publications

References 67 publications

Chemoselective Reactions for the Synthesis of Glycoconjugates from Unprotected Carbohydrates

Chemoselective Reactions for the Synthesis of Glycoconjugates from Unprotected Carbohydrates

Carbohydrate-Based Amphiphiles: Resource for Bio-based Surfactants

Ritter Reaction

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