Über Azidoderivate der Glucose

Bertho, Alfred

doi:10.1002/cber.19300630415

Cited by 45 publications

(11 citation statements)

References 18 publications

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“…59 The glycosyl azides 25 are generally prepared by the reaction of glycosyl halides 24 with NaN 3 in the presence of DMF as the reaction medium. 152 However, synthesis of 25 under this condition requires substantial heat for the reaction to occur; 153 therefore, phase-transfer catalysts are used to facilitate the reaction under milder conditions. 154,155 A straightforward method that avoids the use of 24 for synthesis of clickable azides 25 involves the treatment of acetylated sugars with (TMS)N 3 in the presence of SnCl 4 at room temperature for 24 h (Scheme 8).…”

Section: Azides and Alkyne Substrates: Benefit For Carbohydratesmentioning

confidence: 99%

Cu-Catalyzed Click Reaction in Carbohydrate Chemistry

et al. 2016

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Cu(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition (CuAAC), popularly known as the "click reaction", serves as the most potent and highly dependable tool for facile construction of simple to complex architectures at the molecular level. Click-knitted threads of two exclusively different molecular entities have created some really interesting structures for more than 15 years with a broad spectrum of applicability, including in the fascinating fields of synthetic chemistry, medicinal science, biochemistry, pharmacology, material science, and catalysis. The unique properties of the carbohydrate moiety and the advantages of highly chemo- and regioselective click chemistry, such as mild reaction conditions, efficient performance with a wide range of solvents, and compatibility with different functionalities, together produce miraculous neoglycoconjugates and neoglycopolymers with various synthetic, biological, and pharmaceutical applications. In this review we highlight the successful advancement of Cu(I)-catalyzed click chemistry in glycoscience and its applications as well as future scope in different streams of applied sciences.

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Section: Azides and Alkyne Substrates: Benefit For Carbohydratesmentioning

confidence: 99%

Cu-Catalyzed Click Reaction in Carbohydrate Chemistry

et al. 2016

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“…First we discussed about the widely used method for the preparation of glycosyl azide. Bertho reported the initial work for the preparation of glycosyl azides 142 from acetylated halogenoses, where glycosyl bromide such as 141 , by treatment with sodium azide. This is most commonly used method involving homogeneous one‐phase reactions in DMF and needed elevated temperatures as well as phase‐transfer catalysis that facilitate milder conditions (Scheme ) …”

Section: General Strategy For the Chemical N‐functionalizationmentioning

confidence: 99%

An Overview on the ChemicalN‐Functionalization of Sugars and Formation ofN‐Glycosides

2020

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Its even more than a centennial that the systematic researches of chemical alteration of sugars have been advancing. Out of all the interest in the field of N‐glycoside has assembled pace over the past few years. Therefore, N‐functionalization of sugar is one of the most fundamental modifications along with other group like azide, amide etc also play a remarkable role in the field of glycoscience. Different approaches to access structurally modified N‐glycosides in carbohydrate derivatives are reviewed. The goal of this review is to provide an overview of different way of N‐functionalization of amino sugar and induction of nitrogen scaffolds for the synthesis of various orthogonal protective groups of the N‐glycoside. The N‐functionalization of sugars designate as follows: (a) glycosylamine, (b) glycosyl azide, and (c) introduction of N‐functionality to the sugar for formation of N‐glycosides. This is the first review focus on N‐functionalization of sugars which will be a future scope that influence the readers to work in this area further.

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“…1 While homogeneous one -phase reactions in DMF often require elevated temperatures, 5 phase -transfer catalysis enables milder conditions. 6 One limitation of this methodology is the instability of glycosyl halides.…”

Section: Synthesis Of Azide -Containing Carbohydratesmentioning

confidence: 99%

Azides in Carbohydrate Chemistry

Beckmann

Wittmann

2009

Organic Azides

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I )~.THF.HiO.N~ 2) NB, ~ TI-F . EIOH '''' Schcm c 16.7 SyntheSiS of aminoglycoside derivative 11 using azides as protecting groups for amines. First the amino groups of 18 were converted into azides by diazo /r.lnsfer. l1 After chemical remodeling of the aminoglycoside (one amino group was replaced by a hydroxy grotlp), the amines were regenerated by Stiludinger reduction" 474 Organic Azides: Sylllheses and Applicalions 23 BnO~O BnO~ N °9N'O~N' , 0 0 :1 ~ Cl Y 25 Cl PM~ (1.3 equiv), THF, H~, NaOH 46% PMe3 (1.

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Über Azidoderivate der Glucose

Cited by 45 publications

References 18 publications

Cu-Catalyzed Click Reaction in Carbohydrate Chemistry

Cu-Catalyzed Click Reaction in Carbohydrate Chemistry

An Overview on the ChemicalN‐Functionalization of Sugars and Formation ofN‐Glycosides

Azides in Carbohydrate Chemistry

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