129171-17-1Relevant academic research and scientific papers
Synthesis and reactivity of 4'-deoxypentenosyl disaccharides
Padungros, Panuwat,Fan, Ren-Hua,Casselman, Matthew D.,Cheng, Gang,Khatri, Hari R.,Wei, Alexander
, p. 4878 - 4891 (2014/06/23)
4-Deoxypentenosides (4-DPs) are versatile synthons for rare or higher-order pyranosides, and they provide an entry for structural diversification at the C5 position. Previous studies have shown that 4-DPs undergo stereocontrolled DMDO oxidation; subsequent epoxide ring-openings with various nucleophiles can proceed with both anti or syn selectivity. Here, we report the synthesis of α- and β-linked 4'-deoxypentenosyl (4'-DP) disaccharides, and we investigate their post-glycosylational C5' additions using the DMDO oxidation/ring-opening sequence. The α-linked 4'-DP disaccharides were synthesized by coupling thiophenyl 4-DP donors with glycosyl acceptors using BSP/Tf2O activation, whereas β-linked 4'-DP disaccharides were generated by the decarboxylative elimination of glucuronyl disaccharides under microwave conditions. Both α- and β-linked 4'-DP disaccharides could be epoxidized with high stereoselectivity using DMDO. In some cases, the α-epoxypentenosides could be successfully converted into terminal l-iduronic acids via the syn addition of 2-furylzinc bromide. These studies support a novel approach to oligosaccharide synthesis, in which the stereochemical configuration of the terminal 4'-DP unit is established at a post-glycosylative stage.
Synthesis and evaluation of 3″- and 4″-deoxy and -fluoro analogs of the immunostimulatory glycolipid, KRN7000
Raju, Ravinder,Castillo, Bernard F.,Richardson, Stewart K.,Thakur, Meena,Severins, Ryan,Kronenberg, Mitchell,Howell, Amy R.
supporting information; experimental part, p. 4122 - 4125 (2010/04/29)
Four 3″- and 4″-deoxy and -fluorogalactosyl ceramides were synthesized, and their ability to stimulate iNKT cells, based on levels of IL-2 production, was assessed in three NKT cell receptor hybridomas. In two of the hybridomas, 1.2 and 2H4, all of the analogs were immunostimulatory, while in the 1.4 hybridoma only the 4″-fluoro analog led to the production of significant levels of IL-2.
Chemistry of 4,6-O-benzylidene-D-glycopyranosyl triflates: Contrasting behavior between the gluco and manno series
Crich, David,Cai, Weiling
, p. 4926 - 4930 (2007/10/03)
Activation of either anomer of S-phenyl 2,3-di-O-benzyl-4,6-O- benzylidene-1-deoxy-1-thia-D-glucopyranoside with triflic anhydride in dichloromethane at -78 °C in the presence of 2,6-di-tert-butyl-4- methylpyridine affords a highly active glycosylating species which, on addition of alcohols, provides α-glucosides with high selectivity. This selectivity stands in stark contrast to the analogous mannopyranoside series, which affords the β-mannosides with excellent selectivity under the same conditions. Low-temperature NMR experiments support the notion that a glucosyl triflate is formed in the initial activation step. Possible reasons for the diverging stereoselectivity in the gluco and manno series are discussed.
Synthesis of C-glycopyranosyl compounds by a palladium-catalyzed coupling reaction of 1-tributylstannyl-D-glucals with organic halides
Dubois, Eric,Beau, Jean-Marie
, p. 103 - 120 (2007/10/02)
1-Tributylstannyl-D-glucals, prepared from the corresponding 1-phenylsulfonyl-D-glucals, were coupled efficiently to various organic halides in the presence of a palladium(0) catalyst.This mild reaction is specially useful for the preparation of 1-C-aryl-
Practical synthesis of oligosaccharides. Partial synthesis of avermectin B(1a)
Nicolaou,Dolle,Papahatjis,Randall,Dolle
, p. 4189 - 4192 (2007/10/02)
A practical synthesis of oligosaccharides from phenylthio sugars via glycosyl fluorides is described. The new technology is applied to the synthesis of hexasaccharide 9 from a glucose derivative and avermectin B1a(11) from an avermectin B1
