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DOI: 10.1055/s-2005-861848
Synthesis of Aza-C-disaccharides (Dideoxyimino-alditols C-Linked to Monosaccharides) and Analogues
Publication History
Publication Date:
10 March 2005 (online)
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Abstract
The first aza-C-disaccharide (D-azaMan-β-CH2-(1→6)-d-Man-α-OMe) that mimicks α-d-Manp-(1→6)-α-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 iminoaldoses 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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1 Introduction
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2 Synthesis of Linear Aza-C-disaccharides
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2.1 Miyaura-Suzuki Coupling
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2.2 Samarium Diiodide Barbier Reaction
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2.3 Acetylide Addition to Aldonolactones
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2.4 Intramolecular Oxyalkylation
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2.5 Wittig Olefination
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2.6 Cycloaddition Reactions of Functionalized Nitrones
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3 Synthesis of Branched Aza-C-disaccharides
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3.1 Cross-Aldol Reaction with ‘Naked Sugar’-Derived Ketones
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3.2 Michael Condensation of ‘Naked Sugar’-Derived Enone and Urunolactone
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3.3 Cross-Aldol Reactions with Isolevoglucosenone Derivatives and 2,5-Dideoxy-2,5-iminopentoses
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3.4 Takai-Oshima-Nozaki-Kishi Couplings
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3.5 Miyaura-Suzuki Couplings
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3.6 Dipolar Cycloadditions of Chiral Nitrones
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3.7 Intramolecular Oxyalkylations
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4 Synthesis of Pseudo-aza-C-disaccharides
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5 Synthesis of Homo-aza-C-(1→3)-disaccharides
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6 Conformations of Aza-C-disaccharides
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7 Glycosidase Inhibitory Activities
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8 Conclusion
Key words
aza-C-disaccharides - conformational analysis - cross-glycosidase inhibitors - naked sugars - homo-aza-C-disaccharides - pseudo-aza-C-disaccharides
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