title: Towards inhibitors of glycosyltransferases: A novel approach to the synthesis of 3-acetamido-3-deoxy-D-psicofuranose derivatives.
abstract: A novel synthetic strategy leading to 3-acetamido-3-deoxy-D-psicofuranose 9 is presented. The latter compound, after some manipulations, was transformed into fully protected 3-acetamido-3-deoxy-D-psicofuranose 11 as a potential substrate for the synthesis of N-acetylglucosaminyltransferase inhibitors designed by computational methods. After the attempted thioglycosylation of 11 with EtSH in the presence of BF3·OEt2, 2-methyloxazoline derivatives 13 and 14 were isolated.
authors.affiliation: Institute of Chemistry, Slovak Academy of Sciences, Dúbravská cesta 9, SK-845 38, Bratislava, Slovakia.
authors.forename: Maroš
authors.initials: M
authors.lastname: Bella
authors.affiliation: Institute of Chemistry, Slovak Academy of Sciences, Dúbravská cesta 9, SK-845 38, Bratislava, Slovakia.
authors.forename: Miroslav
authors.initials: M
authors.lastname: Koóš
authors.affiliation: Institute of Biological Chemistry, Academia Sinica, No. 128 Academia Road Sec. 2, Taipei 11529, Taiwan.
authors.forename: Chun-Hung
authors.initials: CH
authors.lastname: Lin
keywords: D-psicofuranose; glycosyltransferases; inhibitors; synthesis; thioglycosylation