- Triethylamine-methanol mediated selective removal of oxophenylacetyl ester in saccharides
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A highly selective, mild, and efficient method for the cleavage of oxophenylacetyl ester protected saccharides was developed using triethylamine in methanol at room temperature. The reagent proved successful against different labile groups like acetal, ketal, and PMB and also generated good yields of the desired saccharides bearing lipid esters. Further, we also observed DBU in methanol as an alternative reagent for the deprotection of acetyl, benzoyl, and oxophenylacetyl ester groups. This journal is
- Rasool, Javeed Ur,Kumar, Atul,Ali, Asif,Ahmed, Qazi Naveed
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p. 338 - 347
(2021/01/29)
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- GLUCOSIDE MONOMER, POLYMERIZATION COMPOSITION COMPRISING THE SAME AND HYDROGEL LENS USING THE SAME
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The present invention relates to a glucoside-based monomer represented by chemical formula 1, a polymeric composition for producing hydrogel comprising the same, and a hydrogel lens using the same. In the chemical formula 1, R_1 to R_4 is hydrogen, an alkyl group of C_1-C_4, or AA, R_6 is hydrogen or an alkyl group of C_1-C_4, at least one of the R_1 to R_4 is BB, R_5 is selected from hydrogen or CC, and m is an integer selected from 0 to 10. According to the present invention, hydrogel lenses having improved wettability can be provided.COPYRIGHT KIPO 2019
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Paragraph 0124-0130
(2019/08/22)
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- Larger laboratory scale synthesis of 5-methyluridine and formal synthesis of its L-enantiomer
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A larger laboratory scale synthesis (>60 g per run) of 5-methyluridine is presented. The critical intermediate 1,2-O-isopropylidene-α-D-ribofuranose was prepared from very cheap D-glucose via D-allose. Its L-enantiomer was obtained from L-arabinose via L-glucose, and also from L-xylose. {figure presented}.
- Thiesen, Luciano J. Hoeltgebaum,Cabral, Nadia,Joselice E Silva, Maria,Bezerra, Gilson,Doboszewski, Bogdan
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p. 249 - 264
(2017/06/19)
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- Synthesis from d-altrose of (5 R,6 R,7 R,8 S)-5,7-dihydroxy-8- hydroxymethylconidine and 2,4-dideoxy-2,4-imino-d-glucitol, azetidine analogues of swainsonine and 1,4-dideoxy-1,4-imino-d-mannitol
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Ring closure of a 3,5-di-O-triflate derived from d-altrose with benzylamine allowed the formation of both monocyclic and bicyclic azetidine analogues of swainsonine.
- Araújo, Noelia,Jenkinson, Sarah F.,Martínez, R. Fernando,Glawar, Andreas F. G.,Wormald, Mark R.,Butters, Terry D.,Nakagawa, Shinpei,Adachi, Isao,Kato, Atsushi,Yoshihara, Akihide,Akimitsu, Kazuya,Izumori, Ken,Fleet, George W. J.
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supporting information; experimental part
p. 4174 - 4177
(2012/10/23)
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- Synthesis of a MUC1-glycopeptide-BSA conjugate vaccine bearing the 3′-deoxy-3′-fluoro-Thomsen-Friedenreich antigen
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A novel MUC1-glycopeptide-BSA conjugate vaccine with a specifically fluorinated Thomsen-Friedenreich antigen side chain at Thr6 was prepared. Preliminary immunological experiments reveal specific binding of the tumor-associated glycopeptide antigen analog by anti-MUC1-mouse antibodies.
- Hoffmann-Roeder, Anja,Johannes, Manuel
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supporting information; experimental part
p. 9903 - 9905
(2011/10/09)
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- Large scale synthesis of the acetonides of l-glucuronolactone and of l-glucose: easy access to l-sugar chirons
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1,2-O-Isopropylidene-α-l-glucurono-3,6-lactone may be synthesized on a 100-200 g scale from cheaply available d-glucoheptonolactone in an overall yield of 94% in four steps via l-glucuronolactone. Subsequent elaboration to l-glucose, diacetone-l-glucose (1,2:5,6-di-O-isopropylidene-α-l-glucofuranose), and monoacetone-l-glucose (1,2-O-isopropylidene-α-l-glucofuranose) allows easy access to a range of l-sugar chirons.
- Weymouth-Wilson, Alexander C.,Clarkson, Robert A.,Jones, Nigel A.,Best, Daniel,Wilson, Francis X.,Pino-González, Maria-Soledad,Fleet, George W.J.
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experimental part
p. 6307 - 6310
(2010/01/18)
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- Sulfuric acid immobilized on silica: an efficient reusable catalyst for the synthesis of O-isopropylidene sugar derivatives
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Sulfuric acid immobilized on silica proved to be an efficient catalyst for the synthesis of O-isopropylidene sugar derivatives from reducing sugars. The method is very simple and economic for large-scale synthesis in which the catalyst is recovered and reused several times. Reactions with d-glucose, d-galactose, d-mannose, l-rhamnose, l-arabinose, d-xylose and l-sorbose led to the formation of the corresponding thermodynamically stable di-O- and/or mono-O-isopropylidene derivatives in good to excellent yields.
- Rajput, Vishal Kumar,Mukhopadhyay, Balaram
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p. 5939 - 5941
(2007/10/03)
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- Photochemical reactions of imidazole-1-sulfonates (imidazylates)
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Imidazylates 1-3 were irradiated in methanol in the presence and in the absence of the electron donor triethylamine. In each case photochemical deprotection occurred in excellent yield to form the partially protected sugar from which the imidazylate was synthesized. Reactions in the presence of triethylamine required much shorter irradiation times.
- Duan, Shaoming,Binkley, Edith R.,Binkley, Roger W.
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p. 391 - 396
(2007/10/03)
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- Butylstannonic acid catalyzed transesterification of carboxylic esters
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Butylstannonic acid is used as catalyst for transesterification of various carboxylic eaters. This method is also applicable to acetylation/deacetylation of alcohols.
- Furlan, Ricardo L. E.,Mata, Ernesto G.,Mascaretti, Oreste A.
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p. 2257 - 2260
(2007/10/03)
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- Mannuronolactone acetonide: Easy access to C-3 OH and C-5 OH of mannose
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The synthesis of D-mannuronolactone acetonide 1 is described from alginic acid and provides an efficient route for the manipulation at C-5 of mannose. Reduction gives a new acetonide of mannose, 1,2-O-isopropylidene-β-D-mannofuranose which, on further acetonation, gives 1,2:5,6-di-O-isopropylidene-β-D-mannofuranose [giving easy access to C-3 OH of mannose] together with a small amount of 1,2:3,5-di-O-isopropylidene-β-D-mannofuranose. Some silylated derivatives of mannuronolactone allow immediate access to the C-6 of mannose. Such intermediates are likely to be of value in the synthesis of derivatives of mannose.
- Watterson, Mark P.,Martin, Angeles,Kruelle, Thomas M.,Estevez, Juan C.,Fleet, George W. J.
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p. 4111 - 4120
(2007/10/03)
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- Enantiospecific Synthesis of the Hexahydrofuran Unit of Erythroskyrine, a Pentaenoyltetramic Acid Metabolite
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A hexahydrofurofuran unit suitably functionalised for incorporation into the synthesis of erythroskyrine has been prepared in homochiral form from diacetone-D-glucose.
- Jones, Raymond C. F.,Tankard, Mark
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p. 765 - 767
(2007/10/02)
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- Further Stereoselective Reductions of 3-O-Hexafuranosyl S-Methyl Dithiocarbonates with Tributyltin Deuteride. A Comment on Mechanism
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The reduction of 1,2:5,6-di-O-isopropylidene-3-O-(methylthio)thiocarbonyl-β-D-altrose, -mannose and -(3-2H)mannose with tributyltin deuteride and hydride leads to highly stereoselective syntheses of 3-deoxy-1,2:5,6-di-O-isopropylidene-β-D-(3-2H)altrose and -(3-2H)mannose.In addition, the reduction of a pair of diastereomeric dithiocarbonates with virtually no stereochemical constraints leads to the same diastereomeric mixture of reduced products, indicating a common radical intermediate for the reduction.
- Fuller, Trevor S.,Stick, Robert V.
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p. 2509 - 2515
(2007/10/02)
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