Journal
TETRAHEDRON LETTERS
Volume 47, Issue 13, Pages 2087-2092Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2006.01.137
Keywords
lipid A mimetics; glycolipids; immunostimulants; TLR4 agonist; vaccine adjuvant; AGP
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An efficient and scalable synthesis of the potent vaccine adjuvant RC-529 (3) and TLR4 agonist CRX-524 (4) is described in eight steps from 1, 3,4,6-tetra-O-acetyl-2-amino-2-benzyloxycarbonyl-2-deoxy-beta-D-glucopyranose (10c) in ca. 25% overall yield. The synthesis features the strategic use of the N-Cbz group for P-glycosylation and the selective N,N,O-triacylation of common advanced intermediate 15 with (R)-3-tetradecanoyloxy or decanoyloxytetradecanoic acid (8, 9) late in the synthesis. A new method for preparing and enhancing the enantiopurity of (R)-3-hydroxytetradecanoic acid (6), a key component of 3 and 4 as well as bacterial lipid A, is also described. (c) 2006 Elsevier Ltd. All rights reserved.
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