The use of levoglucosenone and isolevoglucosenone as templates for the construction of C-linked disaccharides
| ISSN: | 0008-6215 |
|---|---|
| Přístupová URL adresa: | https://explore.openaire.eu/search/publication?articleId=doi_dedup___::58e329c3565866191dedbbcd04a5d5eb https://pubmed.ncbi.nlm.nih.gov/16678805 |
| Rights: | CLOSED |
| Přírůstkové číslo: | edsair.doi.dedup.....58e329c3565866191dedbbcd04a5d5eb |
| Autor: | Yao-Hua Zhu, Raynald Demange, Pierre Vogel, Loay Awad |
| Rok vydání: | 2006 |
| Předmět: |
chemistry.chemical_classification
Steric effects Ketone Bicyclic molecule Carbohydrate chemistry Organic Chemistry Acetal Disaccharide Stereoisomerism General Medicine Bridged Bicyclo Compounds Heterocyclic Disaccharides Biochemistry Combinatorial chemistry Enol Analytical Chemistry chemistry.chemical_compound Glucose chemistry Nucleophile Organic chemistry Combinatorial Chemistry Techniques Antigens Tumor-Associated Carbohydrate Enone |
| Zdroj: | Carbohydrate research. 341(10) |
| ISSN: | 0008-6215 |
| Popis: | Because of their functionalities (enone, ketone, and acetal) and their bicyclic structure (steric factors), levoglucosenone (1,6-anhydro-3,4-dideoxy-beta-D-glycero-hex-3-enopyran-2-ulose) and isolevoglucosenone (1,6-anhydro-2,3-dideoxy-beta-D-glycero-hex-3-enopyran-4-ulose) are useful templates for the convergent and combinatorial synthesis of (1-->2), (1-->3), and (1-->4)-linked C-disaccharides in reactions combining them with sugar-derived carbaldehydes. Synthetic methods relying on conjugate nucleophilic additions of these enones, their combination with aluminum reagents and aldehydes (Baylis-Hillman reaction) and modified Takai-Hiyama-Nozaki-Kishi couplings of enol triflates derived from them with sugar-derived aldehydes are reviewed. Highly stereoselective methods have thus been developed. These allow the generation of disaccharide mimetics with a high molecular diversity. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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