76548-23-7Relevant academic research and scientific papers
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.
Synthesis of sugar isocyanates and their application to the formation of ureido-linked disaccharides
Avalos, Martin,Babiano, Reyes,Cintas, Pedro,Hursthouse, Michael B.,Jimenez, Jose L.,Light, Mark E.,Palacios, Juan C.,Perez, Esther M. S.
, p. 657 - 671 (2007/10/03)
The present work describes a facile and practical route to carbohydrate-based isocyanates, a reactive and appealing family of chiral heterocumulenes, wich can be easily converted into disaccharides and pseudodisaccharides interconnected by urea moieties.
The use of N-alkoxycarbonyl derivatives of 2-amino-2-deoxy-D-glucose as donors in glycosylation reactions
Boullanger, Paul,Jouineau, Martine,Bouammali, Boufelja,Lafont, Dominique,Descotes, Gerard
, p. 151 - 164 (2007/10/02)
1,3,4,6-Tetra-O-acetyl-2-alkoxycarbonylamino-2-deoxy-β-D-glucopyranoses and 3,4,6-tri-O-acetyl-2-alkoxycarbonylamino-2-deoxy-α-D-glucopyranosyl bromides have been used as donors in glycosylation reactions with model alcohols. β-Glycosides were obtained in good yields and with a high degree of 1,2-trans stereoselectivity.An oxazolidone was formed as the main product from the reaction of some of the glucopyranosylbromides with alcohols of low reactivity, but the formation of all products could be interpreted by a strong participation of the alkoxycarbonylamino group.
N-Allyloxycarbonyl derivatives of D-glucosamine as promotors of 1,2-trans-glucosylation in Koenigs-Knorr reactions and in Lewis acid catalysed condensations
Boullanger, Paul,Banoub, Joseph,Descotes, Gerard
, p. 1343 - 1348 (2007/10/02)
The use of suitably blocked D-glucosamine derivatives possessing the N-allyloxyxarbonyl protective group of the amino function represents potential new routes to 1,2-trans-glucosylations.Both 3,4,6-tri-O-acetyl-2-N-allyloxycarbonyl-2-amino-2-deoxy-α-D-glu
The N-allyloxycarbonyl derivative of D-glucosamine: a potent precursor of β-glycosidation.
Boullanger, P.,Descotes, G.
, p. 2599 - 2602 (2007/10/02)
The allyloxycarbonyl protective group of the amino function is a potent precursor of β-D-glucosidation of D-glucosamine and can be selectively removed or preserved in the presence of other usual carbohydrate protective groups.
