A diversity oriented one-pot synthesis of novel iminosugar C-glycosides

Senthilkumar, Soundararasu; Prasad, Sure Siva; Kumar, P. B. Sunil; Baskaran, Sundarababu

doi:10.1039/c3cc48370c

Cited by 37 publications

(16 citation statements)

References 41 publications

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“…Among the preparative methods for glycosylamines, the condensation between a protected hemiacetal and the appropriate amine in moderate to strongly acidic media constitute common experimental conditions. N ‐Benzyl and other N ‐alkyl‐glycosylamines were thus generated in CH 2 Cl 2 in the presence of molecular sieves,1 whereas N ‐benzyl derivatives were also prepared by further addition of p ‐toluenesulfonic acid (PTSA) to the preceding experimental conditions 4c,7b,7f,14. Alternatively TMSOTf is the reagent of choice to prepare the less reactive N ‐carbonylated analogues, but the reaction also works from glycosyl acetates and therefore involves a different mechanism (substitution reaction at the anomeric carbon, glycosylation‐like process) 2,4a,10…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Reactivity of N‐tert‐Butanesulfinyl Glycosylamines

et al. 2015

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Section: Resultsmentioning

confidence: 99%

Synthesis and Reactivity of N‐tert‐Butanesulfinyl Glycosylamines

et al. 2015

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“…Electron-rich aromatic groups [70]: a great diversity of C-aryl iminosugars 24 have been generated from 25 by the general methodology outlined in Scheme 9.…”

Section: N-(benzyl)- and Other N-(alkyl)-n-glycosidesmentioning

confidence: 99%

Glycoside Mimics from Glycosylamines: Recent Progress

Nicolas

Martin

2018

Molecules

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Glycosylamines are valuable sugar derivatives that have attracted much attention as synthetic intermediates en route to iminosugar-C-glycosyl compounds. Iminosugars are among the most important glycomimetics reported to date due to their powerful activities as inhibitors of a wide variety of glycosidases and glycosyltransferases, as well as for their use as pharmacological chaperones. As they provide ready access to these important glycoside mimics, we have reviewed the most significant glycosylamine-based methodologies developed to date, with a special emphasis on the literature reported after 2006. The groups of substrates covered include N-alkyl- and N-benzyl-glycosylamines, N-glycosylhydroxylamines, N-(alkoxycarbonyl)-, and N-tert-butanesulfinyl-glycosylamines.

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“…Recently, the use of carbohydrates has attracted interest in the field of DOS [86][87][88][89] due to their immense potential for generating stereochemical and structural diversity as well as their biomedical applications. [90][91][92] In notable recent work in this area, Trabocchi and colleagues 93 described how building blocks derived from D-mannose and glycine could be used to create the structural complexity following a substrate-based build-couple/pair strategy (Scheme 2.4).…”

Section: Dos As a Tool For The Identification Of New Anticancer Smallmentioning

confidence: 99%

Chapter 2. The Application of Diversity-oriented Synthesis in Chemical Biology

Mateu¹,

Kidd²,

Osberger³

et al. 2018

Chemical Biology

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Communicable and non-communicable diseases are prevalent worldwide. Whilst treatments and cures exist for several of these, for many more they are either ineffective or non-existent. Cancer, malaria and antibiotic resistance are some representative examples of conditions that cause huge burdens on worldwide healthcare. However, despite research and development investment being higher than ever, the biomedical community struggles to provide effective solutions for such devastating diseases. This can be attributed to the inability to identify appropriate targets to modulate the disease, the lack of suitable compounds to interact with identified targets, or the failure of compounds to pass through clinical trials. In such a situation, the question remains as to where the problem fundamentally lies and how to address it. This chapter will analyse the importance of screening

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A diversity oriented one-pot synthesis of novel iminosugar C-glycosides

Cited by 37 publications

References 41 publications

Synthesis and Reactivity of N‐tert‐Butanesulfinyl Glycosylamines

Synthesis and Reactivity of N‐tert‐Butanesulfinyl Glycosylamines

Glycoside Mimics from Glycosylamines: Recent Progress

Chapter 2. The Application of Diversity-oriented Synthesis in Chemical Biology

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