Synthesis of 3e- and 6e-monosulfated and 3e,6e-disulfated lewis x pentasaccharides, candidate ligands for human l-selectin

Article abstract of DOI:10.1080/07328300008544072

Condensation of perbenzyl fucosyl bromide 4 with the known 2-acetamido derivative 1 and with the 2-phthalimido analog 3 gave, respectively, disaccharides 5 and 6 which, after reductive opening of the benzylidene group were glycosylated using peracetylated galactose trichloroacetimidate to give trisaccharides 10 and 11. After removal of the anomeric p-methoxybenzyl group and subsequent activation as the trichloroacetimidate, condensation onto the known lactose derivative 16 afforded protected pentasaccharides 18 and 17 in 24 and 70% yields, respectively. Compound 17 was transformed into 18 by a conventional method in 77% yield making the phthalimido route overall more attractive. The terminal galactose was then selectively deprotected and sulfated at the 3e, 6e and both 3e,6e positions to give the title compounds after complete deprotection.

Full text of DOI:10.1080/07328300008544072

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Synthesis of 3E- And 6E-
Monosulfated and 3E,6E-Disulfated
Lewis X Pentasaccharides, Candidate
Ligands for Human L-Selectin
André Lubineau , Jocelyne Alais & Remy Lemoine
a Institut de Chimie Moléculaire d'Orsay, Laboratoire de
Chimie Organique Multifonctionnelle, CNRS URA 462,
Université de Paris-Sud , F-91405 Orsay cedex, France
Published online: 27 Feb 2008.
To cite this article: André Lubineau , Jocelyne Alais & Remy Lemoine (2000) Synthesis
of 3E- And 6E-Monosulfated and 3E,6E-Disulfated Lewis X Pentasaccharides, Candidate
Ligands for Human L-Selectin, Journal of Carbohydrate Chemistry, 19:2, 151-169, DOI:
10.1080/07328300008544072
To link to this article: http://dx.doi.org/10.1080/07328300008544072
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