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An exploratory study on the synthesis of heparin-like oligosaccharides by polycondensation

AuthorsMartín-Lomas, Manuel; Reichardt, Niels Christian
KeywordsHeparin oligosaccharides
n-pentenyl glycosides
Issue Date11-Mar-2005
PublisherArkat USA
CitationArkivoc: Online Journal of Organic Chemistry 9: 133-135 (2005)
AbstractThe synthesis of heparin oligosaccharide fragments by autocondensation of suitably protected D-glucosamine α1→4 L-iduronic acid disaccharide constructs containing both glycosyl- donor and glycosyl- acceptor functionalities has been explored. Trichloroacetimidate and n-pentenyl groups have been investigated for anomeric activation. The generation of building blocks equipped with a trichloroacetimidate function is seriously hampered by the presence of the free- OH glycosyl- acceptor group on the same molecule, which favors an intramolecular transesterification reaction. Using an n-pentenyl leaving group, the glycosylation promoter competes as a nucleophile with the OH glycosyl acceptor in the autocondensation process, giving rise to fast termination of the chain reaction, a low yield, and low degree of polymerization. It is concluded that, in this area, polycondensation can hardly compete with elaborate stepwise approaches as a result of the intrinsic low reactivity—both as a glycosyl donor and as glycosyl acceptor—of the D-glucosamine α1→4 L-iduronic acid building blocks.
Description13 páginas, 5 esquemas
Publisher version (URL)http://www.arkat-usa.org/get-file/18788/
Appears in Collections:(IIQ) Artículos
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