Synthesis of 10-, 11-and 12-membered chiral benzolactones fused to furanose/pyranose sugars has been achieved in good to excellent yields using an intramolecular Sonogashira reaction. Positions 1-2, 3-5, 3-6 and 5-6 of sugar were utilized for the construction of the macrocycles. The requisite furanose/pyranose scaffolds were synthesized utilising conventional protection-deprotection strate-
Azidotrimethylsilylation of carbohydrates (monosaccharides and disaccharides) has been achieved in high yields under Mitsunobu conditions. The azidation of carbohydrates is effected at 0 °C essentially only at the primary alcoholic position in mono, di- and triols in protected/unprotected glycosides, whereas the remaining secondary hydroxyl groups got silylated. Surprisingly, no azidation of the secondary hydroxyls was observed in all the carbohydrate substrates. Applications of the methodology for the synthesis of amino sugars, triazoles and azasugars are reported.
Regioselective Azidotrimethylsilylation of Carbohydrates and Applications Thereof. -This method uses Mitsunobu conditions and trimethylsilyl azide to substitute primary alcohol moieties of carbohydrates with azide groups while secondary alcohol moieties are silylated. The azide groups of the reaction products can undergo cycloaddition reactions. -(RAO L, M.; YOUSUF, S. K.; MUKHERJEE, D.; TANEJA*, S. C.; Org. Biomol. Chem. 10 (2012) 45, 9090-9098, http://dx.
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