期刊
JOURNAL OF CARBOHYDRATE CHEMISTRY
卷 28, 期 7-8, 页码 395-420出版社
TAYLOR & FRANCIS INC
DOI: 10.1080/07328300903105108
关键词
Heparin; Oligosaccharides; Carbohydrates; Glycosylation; 4-Nitrobenzenesulphonamide protecting group; 2,4-Dinitrophenyl protecting group
资金
- ETH Zurich
- Swiss National Science Foundation
The modular assembly of heparin oligosaccharides requires glucosamine building blocks with amine protecting groups for a-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 a-selective couplings to protected L-iduronic acid derivatives.
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