Synthesis of a novel sialyl lewis X analogue containing a pyrrolidine in place of N-acetyl glucosamine 1

Article abstract of DOI:10.1080/07328300008544095

The synthesis of the new sialyl Lewis X analogue, 4-O-(α-L-fucopyranosyl)-3-O-(3-O-sodium sulfonato-β-D-galactopyranosyl)-(2S,3R, 4R)-2-ethyl-3,4-dihydroxypyrrolidine 2 has been achieved. The N-acetyl glucosamine unit of natural Lewis X has been replaced by a rigid 3R/4R-dihydroxylated pyrrolidine 12. This one has been synthezised from the methyl 4-O-benzoyl-2,3-di-O-benzyl-6-deoxy-6-iodo-α-D-altropyranoside sugar precursor 10 using the Ganem/Bemotas one-pot elimination-reductive amination ring contraction reaction. The (2S,3R,4R)-1-benzyloxycarbonyl-3,4-dihydroxy-2-ethylpyrrolidine 12 obtained was subsequently regioselectively glycosylated, using 2,3,4-tri-O-benzyl-α-L-fucopyranosyl fluoride and 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl bromide as glycosyl donors. Disaccharide containing pyrrolidine 21 was finally transformed into the target O-sulfated analog 2, after regioselective sulfation and usual deprotection.

Full text of DOI:10.1080/07328300008544095

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Synthesis of A Novel Sialyl Lewis X
Analogue Containing A Pyrrolidine in
Place of N-Acetyl Glucosamine
Elsa Dechaux , Pascal Savy , Samule Bouyain , Claude
Monneret & Jean-Claude Florent
a UMR 176, CNRS-Institut Curie, Section Recherche , 26, rue
d'Ulm, F-75248 Paris Cedex 05, France
Published online: 07 Mar 2008.
To cite this article: Elsa Dechaux , Pascal Savy , Samule Bouyain , Claude Monneret & Jean-
Claude Florent (2000) Synthesis of A Novel Sialyl Lewis X Analogue Containing A Pyrrolidine
in Place of N-Acetyl Glucosamine, Journal of Carbohydrate Chemistry, 19:4-5, 485-501, DOI:
10.1080/07328300008544095
To link to this article: http://dx.doi.org/10.1080/07328300008544095
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