Synthesis of Biologically Relevant β‐<i>N</i>‐Glycosides by Biphasic Epoxidation‐Aminolysis of D‐Glycals

Santiago, Cintia C.; Lafuente, Leticia; Ponzinibbio, Agustín

doi:10.1002/slct.202000343

Cited by 6 publications

(1 citation statement)

References 37 publications

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“…In this regard, quite recently, Santiago et al fruitfully synthesized the β-N-glycosides 75 a-f in a two-step approach using oxone as an oxidizing agent (Scheme 20). [62] In the first step, epoxidation of the double bond present in starting compound 72 was performed using the oxone/acetone mixture in ionic liquid 73 which on subsequent aminolysis with the involvement of secondary amines provided the β-N-glycosides 75 a-f in moderate to good yields. The systematic mechanism for this entire two-step protocol is displayed in the Scheme 21.…”

Section: Chemistryselectmentioning

confidence: 99%

Applications of Oxone® in Organic Synthesis: An Emerging Green Reagent of Modern Era

2022

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Presently, the major cornerstone of the research community is to develop green as well as sustainable protocols involving inexpensive catalysts and/or reagents without the usage of hazardous solvents under globally friendlier conditions in order to shelter both mankind and environment. Therefore, needless to say, there is always a supreme need to surrogate the older, costlier and unsafe strategies with the novel economically inexpensive and environmental benign ones. To this context, in recent past, oxone® (triple salt), a very cheap oxidizing agent having the chemical formula 2KHSO5 ⋅ KHSO4 ⋅ K2SO4 and enwrapped with the unique characteristics like easy handling, non‐toxic, safe, eco‐friendly, non‐polluting, stable, and nicely soluble in water, in addition to its utility for large‐scale synthesis etc. Bearing the importance of this versatile reagent in mind, we envisioned to update the recent advances made in this direction. Consequently, in this particular review article, the developments made in the arena of oxone chemistry covering from 2013 to 2020 have been revealed as no report appeared in the literature after a wonderful Chem. Rev. published by the group of Hussain in 2013. Herein, a comprehensive detail of a variety of oxidative transformations along with the complete plausible mechanistic steps have been exposed. For sure, present review would be a very helpful tool to the scientific community not only working in the area of organic synthesis but also to the researchers working in other branches of science and technologies as well.

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Section: Chemistryselectmentioning

confidence: 99%

Applications of Oxone® in Organic Synthesis: An Emerging Green Reagent of Modern Era

2022

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One‐Pot Stereoselective Synthesis of 2,3,4‐Unprotected β‐N‐Glycopyranosides from Glycals and Amines

Gao

Wang

et al. 2023

Adv Synth Catal

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A one‐pot synthesis of 2,3,4‐unprotected β‐N‐glycopyranosides from glycals and amines with exclusive β‐stereoselectivity under room temperature conditions is reported. This method was achieved via palladium‐catalyzed Tsuji‐Trost amination followed by dihydroxylation directly, tolerating anilines, heterocyclic aromatic amines, and N,O‐dimethylhydroxylamine, especially the reaction of primary amines and glycals has not been reported before. Furthermore, the protocol was applied to modify clinical drugs (prazosin, imiquimod) and construct the analogue of the natural product amphimedoside A.

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Synthesis and Structural Characterization of Haloaryl N‐Substituted Sugar Derivatives

Rengel,

Esteche,

Echeverría

et al. 2024

Eur J Org Chem

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We present here the efficient preparation of 6‐N‐haloaryl‐galactosides through a reductive amination process. A complete set of 6‐deoxy‐1,2;3,4‐di‐O‐isopropylidene‐6‐N‐phenylamino‐α‐D‐galactopyranosides were obtained with a straightforward method. The products were structurally analyzed by X‐ray diffraction techniques and NMR spectroscopic data. A complete investigation of the galactosyl derivatives is described, including an unexpected N,N'‐diphenylamino by‐product. Moreover, relevant conformational aspects in solution and in the solid state are identified and discussed.

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Synthesis of Biologically Relevant β‐N‐Glycosides by Biphasic Epoxidation‐Aminolysis of D‐Glycals

Cited by 6 publications

References 37 publications

Applications of Oxone® in Organic Synthesis: An Emerging Green Reagent of Modern Era

Applications of Oxone® in Organic Synthesis: An Emerging Green Reagent of Modern Era

One‐Pot Stereoselective Synthesis of 2,3,4‐Unprotected β‐N‐Glycopyranosides from Glycals and Amines

Synthesis and Structural Characterization of Haloaryl N‐Substituted Sugar Derivatives

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