Recent Advances in the Chemical Synthesis of C-Glycosides
| Autor: | You Yang, Biao Yu |
|---|---|
| Rok vydání: | 2017 |
| Předmět: |
chemistry.chemical_classification
Molecular Structure 010405 organic chemistry Stereochemistry Monosaccharides Chemical glycosylation Glycoside Glycosidic bond General Chemistry 010402 general chemistry 01 natural sciences Chemical synthesis 0104 chemical sciences carbohydrates (lipids) Claisen rearrangement chemistry.chemical_compound chemistry Electrophile Organic chemistry lipids (amino acids peptides and proteins) Glycosyl Glycosides Glycosyl donor |
| Zdroj: | Chemical Reviews. 117:12281-12356 |
| ISSN: | 1520-6890 0009-2665 |
| Popis: | 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-Bäcklund rearrangement, and 1,2-Wittig rearrangement, which usually involve concerted pathways, constitute another category of C-glycosylations. An alternative to the C-glycosylations is the formation of pyranoside/furanoside rings after construction of the predetermined glycosidic C-C bonds, which might involve cyclization of acyclic precursors or D-A cycloadditions. Throughout, the stereoselectivity in the formation of the resultant C-glycosidic linkages is highlighted. |
| Databáze: | OpenAIRE |
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