154618-72-1Relevant academic research and scientific papers
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
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
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.
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.
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
A concise synthesis of the O-glycosylated amino acid building block; using phenyl selenoglycoside as a glycosyl donor
Jiaang, Weir-Torn,Chang, Meng-Yang,Tseng, Ping-Hui,Chen, Shui-Tein
, p. 3127 - 3130 (2007/10/03)
A new glycosylation methodology for synthesizing a protected TF antigen is described. The key step is to use phenyl selenoglycoside as a glycosyl donor, thereby successfully establishing O-linked Fmoc-protected threoninyl monosaccharide in an excellent yi
Synthetic utility of 1,1,2,2-tetraaryIdisilanes: Radical reduction of alkyl phenyl chalcogenides
Yamazaki, Osamu,Togo, Hidco,Yokoyama, Masataka
, p. 2891 - 2896 (2007/10/03)
Reactivity of tetraaryldisilanes as radical reducing agents of alkyl phenyl chalcogenides initiated by Et3B or AIBN was studied. Here, the reactivity of alkyl sulfide was poor; however, various alkyl phenyl selenides and tellurides were reduced to the corresponding hydrocarbons in good yields with 1,1,2,2-tetraphenyldisilane. The Royal Society of Chemistry 1999.
The Use Of Selenophenyl Galactopyranosides for the Synthesis of α- and β-(1->4)-C-Disaccharides
Mallet, Astrid,Mallet, Jean-Maurice,Sinay, Pierre
, p. 2593 - 2608 (2007/10/02)
Methyl α-C-lactoside 4)-α-D-Glcp-OMe> and its α anomer were expeditiously synthesized by radical coupling of various selenophenyl galactopyranosides onto methyl 2,3-di-O-benzyl-4-deoxy-4-C-methylene-α-D-xylo-hexopyranoside, which are tempor
Iodonium Ion-Mediated Glycosidations of Phenyl Selenoglycosides
Zuurmond, H. M.,Klein, P. A. M. van der,Meer, P. H. van der,Marel, G. A. van der,Boom, J. H. van
, p. 365 - 366 (2007/10/02)
Fully benzylated or benzoylated phenyl selenoglycosides can be activated by the promoters iodonium di-sym-collidine perchlorate (IDCP) or N-iodosuccinimide and catalytic triflic acid (NIS/TfOH cat.).The potential of the iodonium ion-mediated glycosidation
