869107-17-5Relevant academic research and scientific papers
A facile method for β-selenoglycoside synthesis using β-p-methylbenzoyl selenoglycoside as the selenating unit
Kawai, Yumiko,Ando, Hiromune,Ozeki, Hideya,Koketsu, Mamoru,Ishihara, Hideharu
, p. 4653 - 4656 (2005)
(Chemical Equation Presented) The reaction between α-glycosyl bromides and potassium p-methylselenobenzoate yields β-p-methylbenzoyl selenoglycosides. The acyl selenoglycosides were activated by the action of a secondary amine and Cs2CO3 to produce an anomeric selenolate anion, which reacted in situ with various electrophiles to yield novel selenoglycosides while retaining the anomeric stereochemistry.
Modular Synthesis of Aryl Thio/Selenoglycosides via the Catellani Strategy
Ding, Ya-Nan,Huang, Yan-Chong,Shi, Wei-Yu,Zheng, Nian,Wang, Cui-Tian,Chen, Xi,An, Yang,Zhang, Zhe,Liang, Yong-Min
supporting information, p. 5641 - 5646 (2021/08/01)
We described a novel palladium-catalyzed domino procedure for the preparation of (hetero)aryl thio/selenoglycosides. Readily available (hetero)aryl iodides and easily accessible 1-thiosugars/1-selenosugars are utilized as the substrates. Meanwhile, 10 types of sugars are quite compatible with this reaction with good regio- and stereoselectivity, high efficiency, and broad applicability (up to 89%, 53 examples). This method enables the straightforward formation of the C(sp2)-S/Se bond of (hetero)aryl thio/selenoglycosides.
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
Stereoselective synthesis of various α-selenoglycosides using in situ production of α-selenolate anion
Nanami, Masahiro,Ando, Hiromune,Kawai, Yumiko,Koketsu, Mamoru,Ishihara, Hideharu
, p. 1113 - 1116 (2007/10/03)
A large variety of α-selenoglycosides, including alkyl and aryl selenoglycosides, selenoglycosyl amino acid and selenodisaccharide have been synthesized in a stereoselective manner. The key precursor of α-anomeric selenolate anion was designed as p-methylbenzoyl selenoglycoside, which was synthesized by the reaction of β-glycosyl chloride with potassium p-methylselenobenzoate. Upon the action of piperazine or methylhydrazine in the presence of Cs2CO3, the acyl selenoglycoside produced an anomeric selenolate anion, which reacted in situ with various electrophilic counterparts to yield α-selenoglycoside.
