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Synthesis of a Conformationally Constrained Heparin‐like Pentasaccharide
Author(s) -
van Boom Jacques H.,
Sakairi Nobuo,
van Der Marel Gijsbert A.,
Basten Jan E. M.,
van Boeckel Constant A. A.
Publication year - 1996
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.19960020817
Subject(s) - chemistry , moiety , iduronic acid , intramolecular force , stereochemistry , acceptor , disaccharide , sulfation , organic chemistry , glucuronic acid , polysaccharide , biochemistry , physics , condensed matter physics
An octasulfated pentasaccharide 1 having an L‐iduronic acid moiety in a fixed 1 C 4 conformation was synthesized by the coupling of a triosyl donor 3 with a disaccharide acceptor 4 followed by deprotection and O ‐sulfation. The acceptor 4 was prepared from the fully acetylated 5‐ C ‐allyl‐β‐ D ‐glucose building block 7 by means of a TMSOTf‐promoted 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.