- Room-Temperature Pd-Catalyzed Synthesis of 1-(Hetero)aryl Selenoglycosides
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A general protocol for functionalization of an anomeric selonate anion at room temperature has been reported. By using the PdG3 XantPhos catalyst, the cross-coupling between the in situ-generated glycosyl selenolate and a broad range of (hetero)aryl and alkenyl iodides furnished a series of functionalized selenoglycosides in excellent yields with perfect control of the anomeric configuration.
- Zhu, Mingxiang,Alami, Mouad,Messaoudi, Samir
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supporting information
p. 6584 - 6589
(2020/09/02)
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- Metal-free synthesis of unsymmetrical organoselenides and selenoglycosides
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A one-pot, metal-free procedure has been developed to synthesize unsymmetrical organoselenides. In the first step of the reaction, arylation of potassium selenocyanate (KSeCN) with an iodonium reagent proceeds in the absence of a metal catalyst to produce
- Guan, Yong,Townsend, Steven D.
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p. 5252 - 5255
(2017/11/06)
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- InBr 3 -Catalyzed Synthesis of Aryl 1,2- trans -Thio(seleno)glycosides
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InBr 3 is demonstrated to be an efficient catalyst for reactions of fully acetated aldoses with aryl mercaptans or selenophenol at room temperature, rapidly furnishing the corresponding thioglycosides or selenoglycosides with exclusively 1,2- t
- Ma, Teng,Li, Changwei,Liang, Haijing,Wang, Zhaoyan,Yu, Lan,Xue, Weihua
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supporting information
p. 2311 - 2314
(2017/10/06)
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- Useful approach to the synthesis of aryl thio- and selenoglycosides in the presence of rongalite
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A simple, mild, and cost effective methodology has been developed for the synthesis of aryl thio-and selenoglycosides from glycosyl halides and diaryl dichalcogenides. Diaryl dichalcogenides undergo reductive cleavage in the presence of rongalite (HOCH2SO2Na) to generate a chalcogenide anion in situ followed by reaction with glycosyl halides to furnish the corresponding aryl thio- and selenoglycosides in excellent yields. Using this protocol, synthesis of 4-methyl-7-thioumbelliferyl-β-d-cellobioside (MUS-CB), a fluorescent non-hydrolyzable substrate analogue for cellulases has been achieved.
- Venkateswarlu, Cheerladinne,Gautam, Vibha,Chandrasekaran, Srinivasan
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- Convenient syntheses of 1,2-trans selenoglycosides using isoselenuronium salts as glycosylselenenyl transfer reagents
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Se-glycosyl-isoselenuronium salts such as three and four which can be prepared in one high-yielding step from acetohalogeno sugars proved to be convenient starting materials for the syntheses of a variety of selenoglycosides. Reaction with (ar)alkyl halid
- Kumar, Ambati Ashok,Illyes, Tuende Zita,Koever, Katalin E.,Szilagyi, Laszlo
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- SELENO-COMPOUNDS AND THERAPEUTIC USES THEREOF
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The present invention relates to compounds and compositions useful as antioxidants and in particular to selenium containing compounds of formula (I): wherein n is 1, 2, or 3; m is 2, 3, 4, or 5; and each R] is independently -(optionally substituted C 1 -C3 alkylene) p-OH, where p is 0 or 1, or a salt thereof. The invention also relates to the use of these seleno-compounds in the treatment of diseases or conditions associated with increased levels of oxidants produced by myeloperoxidase (MPO), such as for instance, atherosclerosis.
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- Odorless eco-friendly synthesis of thio- and selenoglycosides in ionic liquid
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An environmentally benign odorless methodology for the preparation of 1,2-trans-thio- and selenoglycosides is reported. In a one-pot condition, the reductive cleavage of disulfides and diselenides using triethylsilane and borontrifluoride diethyletherate combination followed by the reaction of the in situ generated thiolate and selenoetes with glycosyl acetate derivatives in recyclable room-temperature ionic liquid, [BMIM]BFresulted in excellent yields of thio- and selenoglycosides avoiding the use of obnoxious thiols/selenols and metallic catalysts.
- Sau, Abhijit,Misra, Anup Kumar
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experimental part
p. 1905 - 1911
(2011/10/08)
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- Facile preparation of α-glycosyl iodides by in situ generated aluminum iodide: Straightforward synthesis of thio-, seleno-, and o-glycosides from unprotected reducing sugars
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A facile and practical protocol was developed for the synthesis of glycosyl iodides using AlI3 generated in situ from cheap aluminum metal and molecular iodine. Furthermore, in combination with iodine-catalyzed per-O-acetylation, sequential synthesis of per-acetylated glycosyl iodides, per-acetylated thioglycosides, selenoglycoside, and O-glycosides from unprotected reducing sugars was also achieved with complete diastereocontrol in a one-pot version. Supplemental material is available for this article. Go to the publisher's online edition of Journal of Carbohydrate Chemistry to view the free supplemental file. Copyright Taylor & Francis Group, LLC.
- Weng, Shiue-Shien,Li, Chia-Ling,Liao, Chun-Sheng,Chen, Ting-An,Huang, Chao-Cheih,Hung, Kuo-Tung
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p. 429 - 440
(2012/06/01)
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- Novel approaches for the synthesis and activation of thio- and selenoglycoside donors
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(Chemical Equation Presented) Alkyl thio-, phenyl seleno-, and phenyl thioglycosides can be prepared through short synthetic sequences based on the generation of glycosyl iodides as versatile intermediates. In addition, a novel cheap combined system (stoichiometric NBS and catalytic Bi(OTf)3) has been developed for rapid and efficient activation of a wide variety of thio- and selenoglycoside donors.
- Valerio, Silvia,Iadonisi, Alfonso,Adinolfi, Matteo,Ravida, Alessandra
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p. 6097 - 6106
(2008/02/09)
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- Synthesis of thio- and selenoglycosides by cleavage of dichalconides in the presence of zinc/zinc chloride and reaction with glycosyl bromides
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A convenient odorless methodology has been devised for the preparation of 1,2-trans-thio- and selenoglycosides through zinc-mediated cleavage of disulfides and diselenides and reaction of the thiolate and selenides formed in situ with glycosyl bromides. T
- Mukherjee, Chinmoy,Tiwari, Pallavi,Misra, Anup Kumar
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p. 441 - 445
(2007/10/03)
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- Total synthesis of the Glc3Man N-glycan tetrasaccharide
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The total synthesis of the tetrasaccharide Glcα(1→2)Glcα(1→3)Glcα(1→3)ManαOMe, which corresponds to the terminal tetrasaccharide portion of the glucose terminated arm of the N-glycan tetradecasaccharide, was achieved by the use of differentially protected selenoglycosides and thioglycosides as glycosyl donors, all of which possessed non-participating protection of the 2-hydroxyl group. Favourable anomeric stereoselectivity was achieved for the glycosylation reactions by the use of ether as solvent, or co-solvent. Global deprotection by catalytic hydrogenation with palladium acetate in a mixture of ethanol and acetic acid yielded the target tetrasaccharide.
- Ennis,Cumpstey,Fairbanks,Butters,Mackeen,Wormald
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p. 9403 - 9411
(2007/10/03)
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- Regioselective Lipase-catalysed acylation of 4,6-O-benzylidene-α- and - β-D-pyranoside derivatives displaying a range of anomeric substituents
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The application of Lipase enzymes to effect regioselective C-3-O- acylation of 4,6-O-benzylidene-β-D-gluco- and -galactopyranosides displaying a range of anomeric substituents, and C-2-O-acylation of phenyl 4,6-O- benzylidene-α-D-glucopyranoside and ethyl 4,6-O-benzylidene-1-thio-α-D- glucopyranoside is reported. In particular this method has allowed introduction of a variety of acyl protecting groups at the C-3 hydroxyl group of ethyl 4,6-O-benzylidene-1-thio-β-D-glucopyranoside 11.
- Gridley, Jonathan J.,Hacking, Andrew J.,Osborn, Helen M. I.,Spackman, David G.
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p. 14925 - 14946
(2007/10/03)
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- Regioselective lipase-catalysed acylation of 4,6-O-benzylidene-β-D-pyranoside derivatives displaying a range of anomeric substituents
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The application of lipase enzymes to effect regioselective C-3-O-acylation of 4,6-O-benzylidene-β-D-gluco- and galactopyranosides displaying a range of anomeric substituents is reported. In particular this method has allowed introduction of a variety of acyl protecting groups at the C-3 hydroxyl group of ethyl 4,6-O-benzylidene-1-thio-β-D-glucopyranoside 9.
- Gridley, Jonathan J.,Hacking, Andrew J.,Osborn, Helen M. I.,Spackman, David G.
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p. 1397 - 1399
(2007/10/03)
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- The synthesis of some selenoand telluro-β-d-glucopyranosides
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Several new seleno- and telluro-β-D-glucopyranosides have been prepared by treatment of protected α-D-glucopyranosyl bromides with the appropriate dialkyl or diaryl dichalcogenide and sodium borohydride in ethanol.
- Stick, Robert V.,Tilbrook, D. Matthew G.,Williams, Spencer J.
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p. 233 - 235
(2007/10/03)
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- Novel Glycosidation Methodology. The Use of Phenyl Selenoglycosides as Glycosyl Donors and Acceptors in Oligosaccharide Synthesis
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The use of phenyl selenoglycosides as glycosyl donors and acceptors in glycosidation reactions is described.The versatility of these novel compounds is illustrated by the selective activation of both "disarmed" and "armed" phenyl selenoglycoside donors ov
- Mehta, Seema,Pinto, B. Mario
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p. 3269 - 3276
(2007/10/02)
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