Advances in the chemical synthesis of C-pyranosides/furanosides are summarized, covering the literature from 2000 to 2016. The majority of the methods take advantage of the construction of the glycosidic C—C bond. These C-glycosylation methods are categorized herein in terms of the glycosyl donor precursors, which are commonly used in O-glycoside synthesis and are easily accessible to nonspecialists. They include glycosyl halides, glycals, sugar acetates, sugar lactols, sugar lactones, 1,2-anhydro sugars, thioglycosides/sulfoxides/sulfones, selenoglycosides/telluroglycosides, methyl glycosides, and glycosyl imidates/phosphates. Mechanistically, C-glycosylation reactions can involve glycosyl electrophilic/cationic species, anionic species, radical species, or transition-metal complexes, which are discussed as subcategories under each type of sugar precursor. Moreover, intramolecular rearrangements, such as the Claisen rearrangement, Ramberg–Backlund rearrangement, and 1,2-Wittig rearrangement, which usuall...

Recent Advances in the Chemical Synthesis of C-Glycosides

While natural and synthetic N-nucleosides are vulnerable to enzymatic and acid-catalyzed hydrolysis of the nucleosidic bond, their C-analogues are much more stable. Several C-nucleosides are naturally occurring compounds, e.g., pseudouridine (isolated from the yeast t-RNA) and showdomycin (an antibiotic). Development of novel synthetic methodologies allowed the preparation of a large variety of synthetic analogues, which found numerous applications in medicinal chemistry and chemical biology. Most important biologically active C-nucleosides are the inhibitors of purine nucleosides phosphorylase or IMP dehydrogenase. A number of artificial aryl-C-nucleosides capable of π-stacking are being vigorously investigated as building blocks in chemical biology. In the past few years, several Artificial Expanded Genetic Information Systems (AEGIS)1 have been successfully developed as prime examples of synthetic biology, a newly emerging interdisciplinary area, with the ultimate goal to design systems where high-level behaviors of the living matter are mimicked by artificial chemical systems.2,3

C-nucleosides: synthetic strategies and biological applications.

Recent Advances in the Stereoselective Synthesis of Tetrahydrofurans.

Synthetic routes to 2,5-disubstituted tetrahydrofurans

A convenient, one-step, synthesis of β-C-glycosidic ketones in aqueous media

Recent developments in the synthesis of C-glycosides

Ozonolysis and reductive workup, both at a low temperature, serve to convert alkenyl phenyl selenides into carbonyl compounds that retain the phenylseleno group.

Ozonolysis of olefinic phenyl selenides with preservation of the selenium unit: a route to phenylseleno aldehydes and ketones

A synthetic route from D-glucose to D-myo-inositol-1, 4, 5-tris(dihydrogenphosphate): use of an unusual ene reaction and the Bu2SnCl2/Bu2SnH2 reagent

Recent Developments in the Synthesis of C‐Glycosides

Formal Synthesis of D‐myo‐Inositol 1,4,5‐Tris(dihydrogen phosphate): Cyclization by an Unusual Ene Reaction and Use of the Bu2SnCl2/Bu2SnH2 Reagent for Generating an Equatorial Alcohol.

Maarten H. D. Postema

Papers

Recent developments in the synthesis of C-glycosides

Ozonolysis of olefinic phenyl selenides with preservation of the selenium unit: a route to phenylseleno aldehydes and ketones

A synthetic route from D-glucose to D-myo-inositol-1, 4, 5-tris(dihydrogenphosphate): use of an unusual ene reaction and the Bu2SnCl2/Bu2SnH2 reagent

Recent Developments in the Synthesis of C‐Glycosides

Formal Synthesis of D‐myo‐Inositol 1,4,5‐Tris(dihydrogen phosphate): Cyclization by an Unusual Ene Reaction and Use of the Bu2SnCl2/Bu2SnH2 Reagent for Generating an Equatorial Alcohol.