108782-68-9Relevant academic research and scientific papers
Dioxolanylium Ions Derived from Carbohydrates. X. Nucleophilic trans Opening with the Trichloroacetimidoyl Neighbouring Group
Jacobsen, Steffen
, p. 493 - 497 (2007/10/02)
Oxidation of 3,4-O-benzylidene-galactosan substituted with trichloroacetimidoyl group at O-2 gives a 3,4-fused 1,3-dioxolanylium ion which rearranges to a 2,3-fused 1,3-oxazoline of the gulo configuration, thus bringing about substitution with a nitrogen nucleophile at C-3.Hydrolysis of the resulting relatively stable cyclic trichloroacetimidate under different conditions is shown to give access to a number of selectively protected aminosugar derivatives as well as the free and peracylated compounds.
