Stereoselective synthesis of α-linked 2-deoxysaccharides and furanosaccharides by the use of 2-deoxy 2-pyridyl-1-thio pyrano- and furanosides as donors and methyl iodide as an activator

Article abstract of DOI:10.1016/S0040-4020(01)89016-5

A practical and highly stereoselective glycosidation methodology is described, where anomeric mixture of 2-deoxy 2-pyridyl-1-thiopyranoside donors (1-3,27) have been coupled with several sugar alcohols (4-8,29,31) on activation by methyl iodide to obtain axially linked 2-deoxysaccharides (9-17,30,32,33). Application of this method for the synthesis of disaccharide fragment 28 of avermectin is also described. Utility of this method is also shown by use of 2-pyridyl-1-thiofuranosides (34-36) as donors to prepare α-linked furanosides (42-51).