174741-70-9Relevant academic research and scientific papers
Synthesis of D-fructofuranosides using thioglycosides as glycosyl donors
Krog-Jensen, Christian,Oscarson, Stefan
, p. 1234 - 1238 (1996)
Benzylated and benzoylated ethyl thioglycosides of D-fructofuranose have been synthesized and tested as glycosyl donors in couplings to various primary and secondary carbohydrate acceptors. Treatment of 2-O-acetyl-1,3,4,6-tetra-O-benzoyl-D-fructofuranose with ethyl mercaptan in a BF3·-etherate-promoted reaction gave the benzoylated ethyl 2-thio-α,β-D-fructofuranosides, which after deacylation and benzylation afforded the benzylated derivatives. These thiofructofuranosides, using dimethyl(methylthio)sulfonium triflate (DMTST) or N-iodosuccinimide as promoter, were found to be excellent donors, which gave disaccharide coupling products in quantitative or almost quantitative yields with all tested acceptors, yields rarely found in oligosaccharide synthesis. The benzoylated donors gave only α-linked fructofuranosides, due to participation of the 3-O-benzoyl group, whereas the benzylated donors gave α/β-mixtures.
