260779-99-5Relevant academic research and scientific papers
Prearranged glycosides, 9. - Chemical synthesis of a tetrasaccharide fragment related to the exopolysaccharide of Arthrobacter sp. CE-17
Lemanski, Gregor,Ziegler, Thomas
, p. 181 - 186 (2007/10/03)
The tetrasaccharide 5-aminopentyl glycoside β-D-Manp-(1→4)-β-D-Glcp- (1→4)-α-L-Rhap-(1→3)-β-D-Glcp-1-O-(CH2)5NH2(22) related to the exopolysaccharide of Arthrobacter sp. CE-17 was synthesized by coupling of the properly protected disaccharide blocks β-D-Manp-(1→4)-β-D-Glcp-1-S-Ph (11) and α-L-Rhap-(1→3)-β-D-Glcp-1-O-(CH2)5NHZ (20). Building block 11 was obtained by intramolecular β-mannosylation of a malonyl-tethered disaccharide glycoside which was prepared from phenyl 4,6-O-benzylidene-1- thio-β-D-glucopyranoside (1) and ethyl 2,3,4-tri-O-benzyl-1-thio-α-D- mannopyranoside (5) in 5 steps. Building block 20 was obtained by coupling N- Z-protected 5-aminopentyl 2-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside (14) obtained from the non-benzylated counterpart 12 with ethyl 2,3-di-O- benzoyl-4-O-chloroacetyl-1-thio-α-L-rhamnopyrano- side (18) obtained in 3 steps from ethyl 2,3-O-isopropylidene- 1-thio-α-L-rhamnopyranoside (15).
