Synthesis of Lex and Ley oligosaccharides with azido-type spacer-arms. Comparison of 3- and 4-methoxybenzyl groups as key temporary protective groups

Article abstract of DOI:10.1080/07328309808007459

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 Le^x and Le^y. 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.

Full text of DOI:10.1080/07328309808007459

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Synthesis of LeX and LeY
Oligosaccharides with Azido-Type
Spacer-Arms. Comparison of 3- and 4-
Methoxybenzyl Groups as Key Temporary
Protective Groups
Santiago Figueroa Pérez a , Raul González Lio a , Violeta Fernández
Santana a & Vicente Verez Bencomo a
a Laboratory of Synthetic Antigens, Facultad de Química,
Universidad de La Habana, Ciudad Habana, CUBA, 10400
Version of record first published: 18 Aug 2006.
To cite this article: Santiago Figueroa Pérez, Raul González Lio, Violeta Fernández Santana & Vicente
Verez Bencomo (1998): Synthesis of LeX and LeY Oligosaccharides with Azido-Type Spacer-Arms.
Comparison of 3- and 4-Methoxybenzyl Groups as Key Temporary Protective Groups , Journal of
Carbohydrate Chemistry, 17:6, 835-850
To link to this article: http://dx.doi.org/10.1080/07328309808007459
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