Synthesis of Important Segments of Heparin by Stereoselective Iron(II)-Catalyzed Amidoglycosylation

In this thesis, a stereoselective iron-catalyzed amidoglycosylation reaction is reported, which is

proceed via the N-O bond cleavage of a functionalized hydroxylamine and a novel iron-nitrenoid

intermediate. This method generates exclusive 1,2-cis O-glycosidic linkage between unsaturated

glycosyl donors and acceptors, which is characterized by 1H NMR, TLC-MS, and HSQC. This

thesis focuses on both synthesis of important reaction components and how amidoglycosylation

reactivity is influenced by different combinations of functionalized hydroxylamines, glycosyl

donors, and glycosyl acceptors. These findings are applied to the construction of important

disaccharide units in heparin synthesis, which contributes to a successful and practical synthesis

of heparin building block.