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Synthesis of c glycosyl compounds from 3 4 6 tri o acetyl 1 5 anhydro d arabino hex 1 enitol and allyltrimethylsilane and bistrimethylsilylacetylene



Synthesis of c glycosyl compounds from 3 4 6 tri o acetyl 1 5 anhydro d arabino hex 1 enitol and allyltrimethylsilane and bistrimethylsilylacetylene



Carbohydrate Research 171: 193-200



C-Glycosyl derivatives of compounds bearing two, three, or four carbon atoms were obtained from 3, 4, 6-tri-O-acetyl-1, 5-anhydro-D-arabino-hex-1-enitol (1) via a deacetoxylated oxonium ion generated by treatment with a Lewis acid. The nucleophilic reagents with this cation were bis(trimethylsilyl)acetylene, allyltrimethylsilane, and furan, which were found to exhibit a higher reaction velocity than 1 itself, a potential nucleophile leading to polymerization.

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