Current Organic Chemistry - Current Issue

Perlin’s aldehyde is an α,β-unsaturated carbonyl compound with two well-defined chiral centres and a free hydroxy group. Since its discovery and synthesis by A. S. Perlin in 1975, it has been used as a flexible chiral synthon for synthesising natural products, their scaffolds and biologically significant compounds. Perlin’s aldehydes serve as useful starting materials in diversity-oriented synthesis (DOS) and chiral building blocks in organic synthesis. Currently, synthesising frameworks based on carbohydrates is at the forefront of organic synthesis. Inspired by the reactivity of Perlin’s aldehyde, various research groups worldwide used this molecule as a chiral synthon and published a number of research papers and a review article covering literature until 2012. This review covers recent advances in the synthesis of natural products, their scaffolds and other hetrocylic molecules, starting from perlin aldehyde, covering the literature from 2013 to till date.

Glycosylation reactions are central to carbohydrate chemistry due to their broad applications in drug development and biological probes. Despite presenting significant challenges and often requiring substantial amounts of promoters, these reactions yield value-added products of immense biological importance. The incorporation of transition metal catalysis in glycosylation reactions offers advantages, such as mild reaction conditions and enhanced selectivity. Currently, synthetic chemists are particularly interested in C- and S-glycosides because their glycosidic linkages exhibit greater metabolic stability compared to the more vulnerable O-glycosides. This review aims to explore recent advances in the synthesis of various structurally diverse and biologically relevant C- and S-glycosides, covering literature from 2019 to 2024.

1-Thiosugars and their glycosides play crucial roles in carbohydrate chemistry, primarily due to their stability and potential for mimicking O-glycosides. The synthetic methodologies for thioglycosides pose ongoing challenges. In recent years, researchers have shown a growing interest in exploring the applications of thiosugars in various fields, including the development of natural product derivatives, oligo- and polysaccharide mimics, metallodrugs, and dendrimers. Numerous approaches and protocols have been devised for the synthesis of thiosugars. This review aims to comprehensively cover the efforts towards preparing thiosugars and their application as synthetic precursors.

Due to the compatibility of binding and undergoing chemical modification of sugar derivatives with a variety of scaffolds, the design of innovative tools for bio-sensing and bio-marking, energy harvesting, drug design, and delivery is growing steadily. Furthermore, the chemistry of partially protected sugars has not been explored well in terms of its applications in smart materials. However, these sugar derivatives possess a unique characteristic balance between hydrophilic and hydrophobic nature, which makes them act as gelator molecules. Several synthetic strategies pertaining to synthesis and applications are known in the literature. The present review mainly focuses on the partially protected monosaccharide-based N-glycosylamines and their applications, with few examples from O- and C-glycosides.