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The use of levoglucosenone and isolevoglucosenone as templates for the construction of C-linked disaccharides.
Journal article

The use of levoglucosenone and isolevoglucosenone as templates for the construction of C-linked disaccharides.

  • Awad L Laboratoire de Glycochimie et de Synthèse Asymétrique, Ecole Polytechnique Fédérale de Lausanne (EPFL), BCH, CH-1015 Lausanne, Switzerland. loay.awad@epfl.ch
  • Demange R
  • Zhu YH
  • Vogel P
  • 2006-05-09
Published in:
  • Carbohydrate research. - 2006
Antigens, Tumor-Associated, Carbohydrate
Bridged Bicyclo Compounds, Heterocyclic
Combinatorial Chemistry Techniques
Disaccharides
Glucose
Stereoisomerism
English 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.
Language
  • English
Open access status
closed
Identifiers
Persistent URL
https://roar.hep-bejune.ch/global/documents/225412
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