Synthetic and structural studies of glucosamine derivatives

Siong Tern Liew, Purdue University

Abstract

Glucosamine derivatives are important intermediates in a variety of biologically important oligosaccharides and glycoconjugates. In chapter 1: Chitin-like tetrasaccharide and its 6-O-methyl derivative were synthesized efficiently through trichloroacetimidate-activated glycosylation. A thiophenyl-substituted disaccharide was observed to be an unusually poor glycosyl acceptor in comparison with the corresponding allyloxy-substituted disaccharide. The crystal growth studies and X-ray studies for both tetrasaccharides were investigated. In chapter 2: Orthogonally protected tetrasaccharides were synthesized from protected tetrasaccharides by aminolysis of phthalimide and acetate groups with ethylenediamine, followed by reprotection as a tetraazide. In chapter 3: A novel approach to synthesize L-amino sugars and C-5 modified aminosugars was investigated. Such aminosugars are often found as constituents in a variety of natural products, antibiotics and antitumor agents. The key intermediates, α- and β-2-amino-2,4-dideoxypentenosides, were synthesized from readily available D-glucosamine. Stereoselective epoxidation and ring-opening of 2-amino-2,4-dideoxypentenosides derivatives with different nitrogen-containing functional groups were studied.

Degree

Ph.D.

Advisors

Wei, Purdue University.

Subject Area

Organic chemistry

COinS