Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5279781 | Tetrahedron Letters | 2006 | 6 Pages |
Abstract
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-β-d-glucopyranose (10c) in ca. 25% overall yield. The synthesis features the strategic use of the N-Cbz group for β-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.
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Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Hélène G. Bazin, Laura S. Bess, Mark T. Livesay, Kendal T. Ryter, Craig L. Johnson, Jeffrey S. Arnold, David A. Johnson,