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.


Published in:
Synthesis-Stuttgart, 5, 675-702
Year:
2005
ISSN:
0039-7881
Keywords:
Note:
Univ Sevilla, Fac Quim, Dept Quim Organ, E-41071 Seville, Spain. EPFL, Lab Glycochim & Synth Asymetr, CH-1015 Lausanne, Switzerland.
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Laboratories:




 Record created 2005-11-09, last modified 2018-03-17


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