10163-09-4Relevant articles and documents
Structures of the decomposition products of chlorozotocin: New intramolecular carbamates of 2-amino-2-deoxyhexoses
Hammer,Loranger,Schein
, p. 1521 - 1531 (1981)
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Systematic Structural Characterization of Chitooligosaccharides Enabled by Automated Glycan Assembly
Bordoni, Vittorio,Chaube, Manishkumar A.,Delbianco, Martina,Fittolani, Giulio,Grafmüller, Andrea,Seeberger, Peter H.,Tyrikos-Ergas, Theodore
, p. 2321 - 2325 (2021/01/18)
Chitin, a polymer composed of β(1–4)-linked N-acetyl-glucosamine monomers, and its partially deacetylated analogue chitosan, are abundant biopolymers with outstanding mechanical as well as elastic properties. Their degradation products, chitooligosacchari
New synthesis of glycolipid immunostimulants RC-529 and CRX-524
Bazin, Hélène G.,Bess, Laura S.,Livesay, Mark T.,Ryter, Kendal T.,Johnson, Craig L.,Arnold, Jeffrey S.,Johnson, David A.
, p. 2087 - 2092 (2007/10/03)
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.