Synthesis of aza-C-disaccharides (dideoxyimino-alditols C-linked to monosaccharides) and analogues
The first aza-C-disaccharide (D-azaMan-beta-CHz-(1 -> 6)-D-Man-alpha-OMe) that mimicks alpha-D-Manp-(1 -> 6)-alpha-D-ManOMe was made in 1994 by Johnson and coworkers. Several synthetic approaches to these disaccharide mimetics have been proposed. These are reviewed and compared. Several strategies rely on C-C bond forming reactions such as the Miyaura-Suzuki cross-coupling, the SmI2 Barbier reaction, the addition of acetylides to aldonolactones, the cross-aldol reaction or the Michael addition of 7-oxabicyclo[2.2.1]heptanone derivatives ('naked sugars'), with subsequent formation of the iminoalditol moieties. Other approaches use nitrogen-containing systems such as sugar-derived nitrones or iminoal-doses that are coupled by either Wittig olefinations, cross-aldol reactions or Takai-Oshima-Nozaki-Kishi reactions. When available, the conformational analysis of the aza-C-disaccharides, as well as their inhibitory activities toward glycosidases, will be summarized.
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Keywords: aza-C-disaccharides ; conformational analysis ; cross-glycosidase ; inhibitors ; naked sugars ; homo-aza-C-disaccharides ; pseudo-aza-C-disaccharides ; Alpha-glucosidase inhibitor ; diels-alder reaction ; substituted ; valiolamine derivatives ; treated niddm patients ; oxide cyclo-additions ; protein-bound state ; chiral allyl ethers ; stereoselective-synthesis ; organic-synthesis ; conformational differences
Univ Sevilla, Fac Quim, Dept Quim Organ, E-41071 Seville, Spain. EPFL, Lab Glycochim & Synth Asymetr, CH-1015 Lausanne, Switzerland.
Record created on 2005-11-09, modified on 2016-08-08