Synthetic Pathways to 3,4,5‐Trihydroxypiperidines from the Chiral Pool

Abstract

3,4,5‐Trihydroxypiperidines represent a family of biologically active natural products, found to modulate principally the glycosidase enzymes. This is ascribed to their structural and electronic resemblance to the pyranose monosaccharides, their natural counterparts. Expedient syntheses are crucial to access these valuable high Fsp3 index drug leads. In this review we present the literature strategies to this class of iminosugars to spur further research into drug leads targeting the glycobiological machinery of living systems.

Chiral Graphene Hybrid Materials: Structures, Properties, and Chiral Applications

“…The substantial number of studies also evidence the significant importance of chiral graphene materials. According to specific needs, suitable chiral sources in particular the natural “chiral pool” [ 129–132 ] can be utilized to develop chiral hybrids via reasonable integration with graphene and the derivatives. The “chiral pool” affords numerous possibilities for design and exploitation of novel advanced functional chiral materials.…”

“…In most cases, chiral compounds can be acquired via three ways: 1) natural “chiral pool” (using naturally existing chiral substances to produce new chiral compounds); [ 129–132 ] 2) asymmetric synthesis (as to be addressed below. Ideally, only one enantiomer is generated exclusively; however, this is not true in a major part of the reactions); and 3) chiral switch (switch from the undesired enantiomer to the required one).…”

Developments in Carbohydrate-Based Metzincin Inhibitors

“…Azasugars or iminosugars, whether of natural or synthetic origin, are hydroxylated carbohydrate mimics, where a basic nitrogen substitutes the classic endocyclic oxygen [ 85 ]. This modification appears simple and not significant but provides important biological properties and also gives rise to many synthetic challenges [ 86 , 87 , 88 , 89 , 90 , 91 , 92 ]. Historically, iminosugars are known as inhibitors of glycosidases, enzymes involved in the glycosidic bond hydrolysis in different biological processes, such as intestinal digestion, post-translational processing of the sugar chain of glycoproteins, and lysosomal catabolism of glycoconjugates [ 93 ].…”

Crystal structure of 6-azido-6-deoxy-1,2-O-isopropylidene-α-D-glucofuranose

“…Diminishing the number of synthetic steps to the iminosugar building blocks that are precursors to their alkylated congeners is advantageous. Many iminosugar syntheses start from monosaccharide starting materials (Wood et al, 2018;Lee et al, 2012;Rasmussen & Jensen, 2011). Reducing the number of protecting groups and removing the need for purification by chromatography are useful strategies to a more expedited synthesis of analogues (Katritzky et al, 1991;Liu et al, 2014).…”