1241901-11-0Relevant academic research and scientific papers
A urea-linked glucosamine dimer as a building block for the synthesis of linear and cyclic neosaccharides
Cirillo, Luigi,Silipo, Alba,Bedini, Emiliano,Parrilli, Michelangelo
experimental part, p. 4062 - 4074 (2010/09/18)
A novel urea-linked glucosamine dimer was obtained through a modification of the standard oxazolidinone closure reaction on a 2,3-amino alcohol monomer and fully characterized by NMR spectroscopy and by molecular mechanics and dynamics techniques. A mechanism was proposed for the dimerization reaction that was based on the formation of a 2,3-bis[(p-nitrophenoxy)carbonyl] intermediate, Chemoselective manipulations on the orthogonal protecting group pattern of the dimer - especially on its unprecedented oxazolidinone-urea-oxazolidinone system - gave an alcohol building block that was useful for access to higher linear and cyclic neosaccharides, The conformational features and 3Dcharacterization of a novel carbamate-linked neodisaccharide macrocycle was accomplished through molecular mechanics and dynamics calculations.
