905277-91-0Relevant academic research and scientific papers
Synthesis of pentasaccharide fragments related to the O-specific polysaccharide of Shigella flexneri serotype 1a
Lemanski, Gregor,Ziegler, Thomas
, p. 2618 - 2630 (2006)
The synthesis of the pentasaccharide 5-aminopentyl glycosides α-L-Rhap-(1→3)-[α-D-Glcp-(1→4)]-β-D-GlcpNAc- (1→2)-α-L-Rhap-(1→2)-α-L-Rhap-1-O-(CH2) 5NH2 (29) and α-L-Rhap-(1→3)-α-L-Rhap- (1→3)-[α-D-Glcp-(1→4)]-β-D-GlcpNAc-(1→2) -α-L-Rhap-1-O-(CH2)5NH2 (28), related to the O-specific polysaccharide of Shigella ilexneri serotype 1a by coupling of the suitably protected trisaccharides α-D-Glcp-(1→4)-β-D- Glcp(1→2)-α-L-Rhap-1-O-(CH2)5NH2 (23) and α-L-Rhap-(1→3)-[α-D-Glcp-(1→4)]-β-D-Glcp-1- SPh (26) with the corresponding rhamnosyl glycosides α-L-Rhap-(1→3)- α-L-Rhap-1-SEt (17) and α-L-Rhap-(1→3)-α-L-Rhap-1-O- (CH2)5NH2 (13), is described. Building blocks 23 and 26 were prepared by intramolecular glycosylation of an unsymmetrically tethered cellobiosamine derivative. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.
