1203584-64-8Relevant articles and documents
Synthesis of differentially protected glucosamine building blocks and their evaluation as glycosylating agents
Bindschaedler, Pascal,Dialer, Lukas O.,Seeberger, Peter H.
, p. 395 - 420 (2011/06/19)
The modular assembly of heparin oligosaccharides requires glucosamine building blocks with amine protecting groups for α-selective glycosylations that can be readily removed. The synthesis of N-4-nitrobenzensulphonamide (nosyl)- and N-2,4-dinitrophenyl (DNP)-protected glucosamine building blocks and their evaluation as glycosylating agents is described. The N-nosyl-protected glucosamine building blocks were challenging to prepare and their glycosylations resulted in inseparable mixtures of products. The N-DNP-protected glucosamines, however, were readily synthesized and resulted in α-selective couplings to protected l-iduronic acid derivatives.