23661-29-2Relevant academic research and scientific papers
Room-Temperature Pd-Catalyzed Synthesis of 1-(Hetero)aryl Selenoglycosides
Zhu, Mingxiang,Alami, Mouad,Messaoudi, Samir
supporting information, p. 6584 - 6589 (2020/09/02)
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.
Metal-free synthesis of unsymmetrical organoselenides and selenoglycosides
Guan, Yong,Townsend, Steven D.
, p. 5252 - 5255 (2017/11/06)
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
InBr 3 -Catalyzed Synthesis of Aryl 1,2- trans -Thio(seleno)glycosides
Ma, Teng,Li, Changwei,Liang, Haijing,Wang, Zhaoyan,Yu, Lan,Xue, Weihua
supporting information, p. 2311 - 2314 (2017/10/06)
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
Useful approach to the synthesis of aryl thio- and selenoglycosides in the presence of rongalite
Venkateswarlu, Cheerladinne,Gautam, Vibha,Chandrasekaran, Srinivasan
, p. 48 - 53 (2014/08/18)
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.
SELENO-COMPOUNDS AND THERAPEUTIC USES THEREOF
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, (2012/05/19)
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.
Convenient syntheses of 1,2-trans selenoglycosides using isoselenuronium salts as glycosylselenenyl transfer reagents
Kumar, Ambati Ashok,Illyes, Tuende Zita,Koever, Katalin E.,Szilagyi, Laszlo
, p. 8 - 18 (2012/11/07)
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
Odorless eco-friendly synthesis of thio- and selenoglycosides in ionic liquid
Sau, Abhijit,Misra, Anup Kumar
experimental part, p. 1905 - 1911 (2011/10/08)
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.
Facile preparation of α-glycosyl iodides by in situ generated aluminum iodide: Straightforward synthesis of thio-, seleno-, and o-glycosides from unprotected reducing sugars
Weng, Shiue-Shien,Li, Chia-Ling,Liao, Chun-Sheng,Chen, Ting-An,Huang, Chao-Cheih,Hung, Kuo-Tung
, p. 429 - 440 (2012/06/01)
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.
Novel approaches for the synthesis and activation of thio- and selenoglycoside donors
Valerio, Silvia,Iadonisi, Alfonso,Adinolfi, Matteo,Ravida, Alessandra
, p. 6097 - 6106 (2008/02/09)
(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.
Synthesis of thio- and selenoglycosides by cleavage of dichalconides in the presence of zinc/zinc chloride and reaction with glycosyl bromides
Mukherjee, Chinmoy,Tiwari, Pallavi,Misra, Anup Kumar
, p. 441 - 445 (2007/10/03)
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
