79083-43-5Relevant academic research and scientific papers
Discovery of human hexosaminidase inhibitors by in situ screening of a library of mono- and divalent pyrrolidine iminosugars
Bojarová, Pavla,Carmona, Ana T.,K?en, Vladimír,Kulik, Natalia,Mészáros, Zuzana,Martínez-Bailén, Macarena,Moreno-Vargas, Antonio J.,Pingitore, Valeria,Robina, Inmaculada,Slámová, Kristyna
, (2022/02/14)
Two libraries of mono- and dimeric pyrrolidine iminosugars were synthesized by CuAAC and (thio)urea-bond-forming reactions from the respective azido/aminohexylpyrrolidine iminosugar precursors. The resulting monomeric and dimeric compounds were screened f
Unexpected furanose/pyranose equilibration of N-glycosyl sulfonamides, sulfamides and sulfamates
Suthagar, Kajitha,Polson, Matthew I. J.,Fairbanks, Antony J.
, p. 6573 - 6579 (2015/06/16)
De-protected arabino N-glycosyl sulfamides, sulfonamides and sulfamates were found to mutarotate and convert from the furanose to the thermodynamically more stable pyranose form in aqueous solution. The presence of a strongly electron withdrawing group in
Anodic coupling reactions and the synthesis of C-glycosides
Xu, Guoxi,Moeller, Kevin D.
supporting information; experimental part, p. 2590 - 2593 (2010/08/22)
A convenient, two-step procedure has been developed for converting sugar derivatives into C-glycosides containing a masked aldehyde functional group. The chemistry takes advantage of an anodic coupling reaction between an electron-rich olefin and an alcohol. The sequence works for the formation of both furanose and pyranose derivatives if less polarized vinyl sulfide derived radical cation intermediates are used. With more polarized enol ether derived radical cations, the cyclizations work best for the formation of furanose derivatives where the rate of five-membered ring formation precludes elimination reactions triggered by the radical cation.
Synthesis and properties of triplex-forming oligonucleotides containing 2′-O-(2-methoxyethyl)-5-(3-aminoprop-1-ynyl)-uridine
Lou, Chenguang,Xiao, Qiang,Brennan, Lavinia,Light, Mark E,Vergara-Irigaray, Nuria,Atkinson, Elizabeth M.,Holden-Dye, Lindy M.,Fox, Keith R.,Brown, Tom
experimental part, p. 6389 - 6397 (2010/10/05)
2′-O-(2-Methoxyethyl)-5-(3-aminoprop-1-ynyl)-uridine phosphoramidite (MEPU) has been synthesized from d-ribose and 5-iodouracil and incorporated into triplex-forming oligonucleotides (TFOs) by automated solid-phase oligonucleotide synthesis. The TFOs gave very high triplex stability with their target duplexes as measured by ultraviolet/fluorescence melting and DNase I footprinting. The incorporation of MEPU into TFOs renders them resistant to degradation by serum nucleases.
Synthesis of β-D-ribofuranosyl-(1→3)-α-L-rhamnopyranose by in situ activating glycosylation using 1-OH sugar derivative and Me3SiBr-CoBr2-Bu4NBr-molecular sieves 4A system
Hirooka,Mori,Sasaki,Koto,Shinoda,Morinaga
, p. 1679 - 1694 (2007/10/03)
Β-D-Ribofuranosyl-(1→3)-α-L-rhamnopyranosyl-(1→3)- L-rhamnopyranose, the trisaccharide repeating unit of the C. freundii O28, 1c O-specific polysaccharide, was synthesized using in situ activating glycosylation of the 1-OH sugar derivatives and a reagent mixture of trimethylsilyl bromide, cobalt(II) bromide, tetrabutylammonium bromide, and molecular sieves 4A. Regioselective tritylation was useful for synthesizing the 3-OH derivatives of methyl, allyl, and benzyl α-L-rhamnosides.
Stereoselective syntheses of α-D- and β-D-ribofuranosides catalyzed by the combined use of silver salts and their partners
Shimomura,Mukaiyama
, p. 2532 - 2541 (2007/10/02)
α-D-Ribofuranosides are stereoselectively synthesized in high yields from 2,3,5-tri-O-benzyl-1-O-iodoacetyl-D-ribofuranose (1) and trimethylsilylated nucleophiles by the use of silver salts in the coexistence of 3 molar amounts of lithium perchlorate, whi
An Efficient Method for the Stereoselective Synthesis of β-D- and α-D-Ribofuranosides from 2,3,5-Tri-O-benzyl-D-ribofuranose by the Use of oxotitanium and Trifluoromethanesulfonic Anhydride
Suda, Shinji,Mukaiyama, Teruaki
, p. 1211 - 1215 (2007/10/02)
β-D-Ribofuranoside are stereoselectively synthesized in high yields directly from 2,3,5-tri-O-benzyl-D-ribofuranose and trimethylsilylated nucleophiles by the use of oxotitanium and trifluoromethanesulfonic anhydride, while α-D-ribof
Stereoselective Glycosylation Reaction Starting from 1-O-Trimethylsilyl Sugars by Using Diphenyltin Sulfide and a Catalytic Amount of Active Acidic Species
Mukaiyama, Teruaki,Matsubara, Koki
, p. 1041 - 1044 (2007/10/02)
1,2-trans-Ribofuranosides are stereoselectively synthesized from 1-O-trimethylsilyl ribofuranose and trimethylsilyl ethers in the presence of a catalytic amount of Me3SiOTf using Ph2Sn=S as an additive, while 1,2-cis-ribofuranosides and 1,2-cis-glucopyran
Stereoselective Synthesis of 1,2-trans-Ribofuranosides from 1-Hydroxy Sugars by the Use of oxotitanium and Trifluoromethanesulfonic Anhydride
Suda, Shinji,Mukaiyama, Teruaki
, p. 431 - 434 (2007/10/02)
A convenient method for stereoselective synthesis of 1,2-trans-ribofuranosides directly from 1-hydroxy sugars and alcohols or trimethylsilylated nucleophiles by the use of oxotitanium and trifluoromethanesulfonic anhydride is
An Efficient Method for the Stereoselective Synthesis of 1,2-cis- and 1,2-trans-Ribofuranosides from 1-Hydroxy Ribofuranose by the Use of Diphenyltin Sulfide and Trifluoromethanesulfonic Anhydride
Mukaiyama, Teruaki,Matsubara, Koki,Suda, Shinji
, p. 981 - 984 (2007/10/02)
1,2-trans-Ribofuranosides are stereoselectively synthesized in high yields directly from 1-hydroxy ribofuranose and trimethylsilylated nucleophiles by the use of diphenyltin sulfide and trifluoromethanesulfonic anhydride.Even further, in the coexistence o
