Collect. Czech. Chem. Commun. 2003, 68, 1264-1274

Improved Synthesis of 1,2-trans-Acetates and 1,2-trans Ethyl 1-Thioglycosides Derived from 3,4,6-Tri-O-acetyl-2-deoxy-2-phthalimido-D-hexopyranosides

Jan Veselýa, Miroslav Ledvinab,*, Jindřich Jindřicha, David Šamanb and Tomáš Trnkaa

a Department of Organic Chemistry, Charles University, Albertov 2030, 128 40 Prague 2, Czech Republic
b Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo nám. 2, 166 10 Prague 6, Czech Republic


Effective one-pot synthesis of 1,2-trans-acetates 4b, 5b and 6a derived from N-phthaloyl-protected D-glucosamine, D-galactosamine and D-mannosamine, respectively, is presented. Anomerisation of the corresponding 1,2-cis-acetates 4a, 5a and 6b and direct conversion of all of them to 1,2-trans ethyl 1-thioglycosides 7, 8 and 9 are also described and discussed.

Keywords: Carbohydrates; Aminosugars; Thioglycosides; Glycosyl donors; Phthalimide; Anomerisation; Protecting groups; Glycosides; Glycoconjugates.

References: 25 live references.