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Glycoside Mimics from Glycosylamines: Recent Progress.

Cyril Nicolas¹, Olivier R Martin²

¹Institute of Organic and Analytical Chemistry, UMR 7311, University of Orleans and CNRS, Rue de Chartres, BP 6759, 45067 Orleans CEDEX 2, France. cyril.nicolas@univ-orleans.fr.

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Summary

Glycosylamines are key intermediates for creating iminosugars, which are vital glycomimetics. This review highlights recent glycosylamine-based methods for synthesizing these important sugar mimics.

Keywords:

addition reactions glycomimetics glycosylamines iminosugar-C-glycosides

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Area of Science:

Carbohydrate Chemistry
Medicinal Chemistry
Organic Synthesis

Background:

Glycosylamines are versatile sugar derivatives utilized in organic synthesis.
Iminosugars are crucial glycomimetics with significant biological activities, including enzyme inhibition and chaperone functions.
The development of efficient synthetic routes to iminosugars is of great interest in medicinal chemistry.

Purpose of the Study:

To review significant glycosylamine-based methodologies for synthesizing iminosugar-C-glycosyl compounds.
To focus on literature published after 2006, highlighting recent advancements.
To cover a range of glycosylamine substrates.

Main Methods:

Literature review of glycosylamine-based synthetic methodologies.
Emphasis on methods developed since 2006.
Categorization of reviewed substrates including N-alkyl-, N-benzyl-glycosylamines, N-glycosylhydroxylamines, N-(alkoxycarbonyl)-, and N-tert-butanesulfinyl-glycosylamines.

Main Results:

Glycosylamines provide efficient access to iminosugar mimics.
Recent methodologies have expanded the scope and efficiency of glycosylamine-based synthesis.
Diverse functionalized glycosylamines serve as valuable precursors.

Conclusions:

Glycosylamine-based strategies are essential for the synthesis of iminosugars.
Continued research in this area promises further advancements in accessing novel glycomimetics.
The reviewed methodologies offer valuable tools for synthetic chemists in carbohydrate and medicinal chemistry.