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Highly efficient one-pot synthesis of 1,2,3-triazole-linked glycoconjugates was presented involving a Cu(I) catalyzed 1,3-dipolar cycloaddition as the key step. It offers a convenient route to prepare neoglycoconjugates derived from unprotected saccharides or peracetylated saccharides.
1,3-Dipolar cycloaddition of a (−)-menthone-derived nitrone to allyl bromide under microwave irradiation afforded, stereoselectively, the corresponding chiral isoxazolidine in 98% yield. After substitution of the bromine atom by an azide group (98% yield), another 1,3-cycloaddition with various alkynes led to a series of 1,2,3-triazolyl-functionalized isoxazolidines (∼85% yield). Removal of the chiral...
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