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

Carbohydr Res. 2006 Jul 24;341(10):1235-52. doi: 10.1016/j.carres.2006.04.008. Epub 2006 May 6.

Abstract

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.

Publication types

  • Review

MeSH terms

  • Antigens, Tumor-Associated, Carbohydrate / chemistry
  • Bridged Bicyclo Compounds, Heterocyclic / chemistry*
  • Combinatorial Chemistry Techniques
  • Disaccharides / chemical synthesis*
  • Glucose / analogs & derivatives*
  • Glucose / chemistry
  • Stereoisomerism

Substances

  • 1,6-anhydro-2,3-dideoxyhex-3-enopyran-4-ulose
  • Antigens, Tumor-Associated, Carbohydrate
  • Bridged Bicyclo Compounds, Heterocyclic
  • Disaccharides
  • Thomsen-Friedenreich antigen
  • 1,6-anhydro-3,4-dideoxyhex-3-enopyran-2-ulose
  • Glucose