4981-97-9Relevant academic research and scientific papers
Stereoretentive Reactions at the Anomeric Position: Synthesis of Selenoglycosides
Zhu, Feng,O'Neill, Sloane,Rodriguez, Jacob,Walczak, Maciej A.
supporting information, p. 7091 - 7095 (2018/05/29)
Reported is the stereospecific cross-coupling of anomeric stannanes with symmetrical diselenides, resulting in the synthesis of selenoglycosides with exclusive anomeric control. The reaction proceeds without the need for directing groups and is compatible
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
Photoinitiated glycosylation at 350 nm
Cumpstey, Ian,Crich, David
experimental part, p. 469 - 485 (2012/06/15)
A method for photochemical activation of glycosyl donors is presented. Selenoglycosides were activated by single-electron transfer using a photooxidant, N-methylquinolinium hexafluorophosphate, as photosensitizer and a toluene cosolvent as cosensitizer under irradiation at 350 nm. In this way we were able to synthesize glycosides including (1→6)-linked disaccharides. Benzyl ethers and benzoate esters were compatible with these conditions, allowing potentially synthetically useful transformations. The major by-products were due to hydrolysis; the reactions required the presence of oxygen and were run in air.
Selective activation of glycosyl donors utilising electrochemical techniques: A study of the thermodynamic oxidation potentials of a range of chalcoglycosides
France, Robert R.,Rees, Neil V.,Wadhawan, Jay D.,Fairbanks, Antony J.,Compton, Richard G.
, p. 2188 - 2194 (2007/10/03)
A series of six chalcoglycosides (phenyl-2,3,4,6-tetra-0-benzoyl-1-seleno-β-D-glucopyranoside, phenyl-2,3,4,6-tetraO-benzyl-1-seleno-β-D-glucopyranoside, phenyl-2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside, p-tolyl-2,3,4,6-O-benzoyl-1-thio-β-D-glucop
Highly diastereoselective radical cyclization of a glucose-derived enol ether radical cation/phosphate anion pair
Crich, David,Suk, Dae-Hwan,Sun, Sanxing
, p. 2861 - 2864 (2007/10/03)
Diastereomeric 3-O-allyl-4,6-O-benzylidene-2-O-(diphenylphosphatoxy) β-D-gluco- and β-D-manno-pyranosyl phenylselenides were prepared and subjected to treatment with tributyltin hydride and AIBN. The gluco-compound undergoes smooth radical cyclization to
Total synthesis of the Glc3Man N-glycan tetrasaccharide
Ennis,Cumpstey,Fairbanks,Butters,Mackeen,Wormald
, p. 9403 - 9411 (2007/10/03)
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.
Regioselective Lipase-catalysed acylation of 4,6-O-benzylidene-α- and - β-D-pyranoside derivatives displaying a range of anomeric substituents
Gridley, Jonathan J.,Hacking, Andrew J.,Osborn, Helen M. I.,Spackman, David G.
, p. 14925 - 14946 (2007/10/03)
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.
Regioselective lipase-catalysed acylation of 4,6-O-benzylidene-β-D-pyranoside derivatives displaying a range of anomeric substituents
Gridley, Jonathan J.,Hacking, Andrew J.,Osborn, Helen M. I.,Spackman, David G.
, p. 1397 - 1399 (2007/10/03)
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.
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
