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Synthesis of a Conformationally Constrained Heparin-like Pentasaccharide

✍ Scribed by Prof. Dr. Jacques H. van Boom; Dr. Nobuo Sakairi; Dr. Gijsbert A. van Der Marel; Jan E. M. Basten; Constant A. A. van Boeckel

Publisher: John Wiley and Sons
Year: 1996
Tongue: English
Weight: 868 KB
Volume: 2
Category: Article
ISSN: 0947-6539
DOI: 10.1002/chem.19960020817

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✦ Synopsis

An octasulfated pentasaccharide 1 having an L-iduronic acid moiety in a fixed 'C, conformation was synthesized by the coupling of a triosyl donor 3 with a disaccharide acceptor 4 followed by deprotection and 0-sulfation. The acceptor 4 was prepared from the fully acetylated S-C-allyI-/?-D-glucose building block 7 by means of a TMSOTfpromoted glycosylation, intramolecular substitution and ozonolysis of the olefinic bond as the key reactions. Compound 1 showed very low activity in an antithrombin 111-mediated anti-Xa assay; this reflects the importance of the presence of a flexible L-iduronic acid moiety in heparin-like antithrombotics.

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