Journal of Carbohydrate Chemistry p. 835 - 850 (1998)
Update date:2022-07-30
Topics: Synthesis Comparison Experimental Oligosaccharides Azido-type spacer-arms Protective groups 3and 4-methoxybenzyl groups
Figueroa Pérez, Santiago
González Lio, Raul
Fernández Santana, Violeta
Verez Bencomo, Vicente
5-Azido-3-oxa-1-pentanol was prepared from 2-(2-chloroethoxy)ethanol and used as a spacer in the chemical synthesis of the trisaccharide β-D-Gal-(1→4)-[α-L-Fuc-(1-→3)]-GlcNAc and the tetrasaccharide α-L-Fuc-α-(1→2)-β-D-Gal-(1→4)-[α-L-Fuc- (1→3)]-GlcNAc that represent the epitopes defining the human blood groups Lex and Ley. The classical 4-methoxybenzyl group and the remarably acid-stable 3-methoxybenzyl group were compared as temporary protective groups for position 3 at the glucosamine unit to circumvent the problems associated with the simultaneous presence of allyl and azido groups. The resulting oligosaccharides were coupled to proteins with high efficiency.
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