287962-77-0Relevant academic research and scientific papers
Synthesis of 1,3- and 2,3-diglycosylated indoles as potential trisaccharide mimetics
Wiebe, Christine,Fust De La Sotilla, Silvia,Opatz, Till
, p. 1385 - 1397 (2012/07/13)
Diglycosylated heteroaromatics may serve as metabolically stable mimetics of trisaccharides. Herein, the preparation of several 1,3- and 2,3-diglycosylindoles by direct C-glycosylation of monoglycosylated precursors is described. Georg Thieme Verlag Stuttgart ? New York.
Sweet (hetero)aromatics: Glycosylated templates for the construction of saccharide mimetics
Wiebe, Christine,Schlemmer, Claudine,Weck, Stefan,Opatz, Till
, p. 9212 - 9214 (2011/10/04)
Mono- and diglycosylated aromatics and heteroaromatics may serve as building blocks for the construction of metabolically stable mimetics of oligosaccharides. Methods for their preparation from monosaccharidic precursors by direct C-glycosylation, dipolar cycloaddition or Larock cyclization are described.
Synthesis of 1,2,3-triazole linked galactopyranosides and evaluation of cholera toxin inhibition
Leaver, David J.,Dawson, Raymond M.,White, Jonathan M.,Polyzos, Anastasios,Hughes, Andrew B.
, p. 8465 - 8474 (2012/04/23)
We report the synthesis of a series of bivalent 1,2,3-triazole linked galactopyranosides as potential inhibitors of cholera toxin (CT). The inhibitory activity of the bivalent series was examined (ELISA) and the series showed low inhibitory activity (millimolar IC50s). Conversely, the monomeric galactotriazole analogues were strong inhibitors of cholera toxin (IC 50 = 71-75 μM). The Royal Society of Chemistry 2011.
Synthesis of immunostimulatory α- C -galactosylceramide glycolipids via sonogashira coupling, asymmetric epoxidation, and trichloroacetimidate- mediated epoxide opening
Liu, Zheng,Byun, Hoe-Sup,Bittman, Robert
supporting information; experimental part, p. 2974 - 2977 (2010/11/16)
Stereocontrolled syntheses of α-C-GalCer (2) and its α-C-acetylenic analogue 6 were accomplished in high efficiency by a convergent construction strategy from 1-hexadecene and d-galactose. The key transformations include Sonogashira coupling, Sharpless asymmetric epoxidation, and Et2AlCl-catalyzed cyclization of an epoxytrichloroacetimidate to generate protected dihydrooxazine 21.
A concise synthesis of (3S,4S,5R)-1-(α-d-galactopyranosyl)-3- tetracosanoylamino-4,5-decanediol, a C-glycoside analogue of immunomodulating α-galactosylceramide OCH
Toba, Tetsuya,Murata, Kenji,Yamamura, Takashi,Miyake, Sachiko,Annoura, Hirokazu
, p. 5043 - 5047 (2007/10/03)
A concise and convergent synthesis of the C-glycoside analogue 2b of immunomodulating α-galactosylceramide OCH 1b starting from readily available 2,3,4,6-tetra-O-benzyl-d-galactose 3 and l-arabinose 6 is described. The synthesis features the nucleophilic addition of an α-ethynyl sugar 5 to the phytosphingosine-precursor aldehyde 9 and would be applicable to a variety of C-glycoside analogues of interest.
Novel synthetic C-glycolipids, their synthesis and use to treat infections, cancer and autoimmune diseases
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, (2010/02/14)
The invention is directed to novel compounds of formulae (I), (II) and (III): wherein X is O or NH; R3 is OH or a monosaccharide and R4 is hydrogen, or R3 is hydrogen and R4 is OH or a monosaccharide; R5 is hydrogen or a monosaccharide; and pharmaceutically acceptable salts or esters thereof. The invention is also directed to the use of the compounds both directly and as immune adjuvants for treating cancer, infectious diseases and autoimmune diseases. The invention is also directed to syntheses of the intermediates which can be used to make these novel compounds.
Stereocontrolled syntheses of α-C-mannosyltryptophan and its analogues
Nishikawa, Toshio,Koide, Yuya,Kajii, Shigeo,Wada, Kyoko,Ishikawa, Miyuki,Isobe, Minoru
, p. 687 - 700 (2007/10/03)
The total synthesis of α-C-mannosyltryptophan (C-Man-Trp), a naturally occurring C-glycosylamino acid, was achieved from a commercially available α-methyl-D-mannoside in 10 steps including the following key steps: the C-glycosidation of a mannose derivative with a stannylacetylene, Castro indole synthesis, and Sc(ClO4)3-promoted coupling with L-serine-derived aziridine carboxylate. The glucose- and galactose-analogues of C-Man-Trp were also synthesized in a similar manner. Conformational analyses of the synthesized C-glycosyltryptophan and its synthetic intermediate are briefly discussed.
Synthesis of α- and β-glycosyl asparagine ethylene isosteres (C-glycosyl asparagines) via sugar acetylenes and Garner aldehyde coupling
Dondoni, Alessandro,Mariotti, Giandomenico,Marra, Alberto
, p. 4475 - 4486 (2007/10/03)
A convergent approach has been developed for the synthesis of C-glycosyl amino acids in which the glycinyl moiety CH(NH2)CO2H is connected to the anomeric center of the sugar residue by a three carbon atom tether. Essentially, these compounds are isosteres of N-glycosyl asparagines in which the amide group has been replaced by an ethylene bridge. Following the coupling of α- or β-D-linked lithium C-glycoside acetylides with N-Boc D-serinal acetonide (Garner aldehyde), the resulting adducts were transformed into the final N-Boc-C-glycosyl-α-aminopentanoic acids via reduction of the triple bond, deoxygenation, and oxidative cleavage of the oxazolidine ring. By this protocol, 12 C-glycosyl asparagines, six pairs of α- and β-anomers, have been prepared incorporating the gluco, galacto, manno, and the corresponding 2-acetamido-2-deoxy residues.
General, stereoselective synthesis of ethylene isosteres of α- and β- glycosylasparagines
Dondoni, Alessandro,Mariotti, Giandomenico,Marra, Alberto
, p. 3483 - 3487 (2007/10/03)
The coupling of α- or β-D-linked lithium C-glycosyl acetylides with N- Boc D-serinal acetonide followed by the reduction of the triple bond, deoxygenation, and oxidative cleavage of the oxazolidine ring afforded α- and β-anomer pairs of C-glycosyl α-aminopentanoic acids (gluco, manno, galacto, and 2-acetamido-galacto). (C) 2000 Elsevier Science Ltd.
