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

Abstract

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.

Self‐Promoted Glycosylation for the Synthesis of β‐N‐Glycosyl Sulfonyl Amides

“…[2] Glycosyl amides are generally synthesized from the glycosyl amines via glycosyl azides, which after reduction is used as the coupling partner to the activated carboxylic acid derivative. [3] There are however two major problems with this approach. Firstly the undesired anomerization of the glycosyl amine to give the α-anomer [4] and secondly the activated aspartic acid in the peptide chain, which is the precursor for the N-glycosylated asparagine, can cyclize to give the undesired aspartimide.…”

Synthesis of 1,4‐Disubstituted 1,2,3‐Triazoles from Terminal Vinyl Sulfones in Ionic Liquid: A Metal‐Free Eliminative Azide‐Olefinic Cycloaddition Route to Triazolyl Carbohydrates and Triazole‐linked Bissaccharides

“…The reaction patterns of non‐carbohydrate internal vinyl sulfones are depicted in Scheme 1 (A and B), which suggests that comparatively electron‐neutral groups (e. g. aryl, alkyl) would provide 1,5‐DTs (Scheme 1A) [15] whereas, electron withdrawing groups (e. g. CO 2 Me) would mostly afford 1,4‐DTs (Scheme 1B) [14] . These observations were equally applicable to carbohydrate derivatives and therefore vinyl sulfone‐modified carbohydrates, on one hand afforded a plethora of 1,5‐DTs, 1,5‐DT‐modified carbohydrates and several 1,5‐DT linked bissacharides under metal‐free conditions [13,16] …”

A facile synthesis of amphiphilic N-glycosyl naphthalimides and fabrication of flexible semiconductors using molecular self-assembly

“…[20][21][22][23][24] Among the various glycosides reported in the literature, N-glycosides received a special attention among the researchers because of their existence as an important component in DNA, RNA, cofactors, and a large variety of signalling molecules. 25,26 By considering the salient feature of N-glycosides in the fields of pharmaceutical science and molecular materials, in this paper, we have synthesized a library of N-glycosides from monosaccharides, generally referred to as a chiral pool, and naphthalimides. The selection of naphthalimide as the aglycon part is due to the presence of highly conjugated systems and the existence of immense pharmacological properties.…”