259827-51-5Relevant articles and documents
Synthesis of C-spiro-glycoconjugates from sugar lactones via zinc mediated Barbier reaction
Lambu, Mallikharjuna Rao,Hussain, Altaf,Sharma, Deepak K.,Yousuf, Syed Khalid,Singh, Baldev,Tripathi, Anil. K.,Mukherjee, Debaraj
, p. 11023 - 11028 (2014/03/21)
Anomeric gem-diallylation, mono-β-crotylation and mono-β- propargylation of sugar 1,5 and 1,4 lactones have been achieved under Barbier reaction conditions using Zn powder and a catalytic amount of TMSCl as an activator. Ring closing olefin metathesis of the synthesized gem-diallyl derivatives furnished C-spiro cyclopentene glycosides. Finally, the cyclopentene rings were converted into carbohydrate based tricyclic morpholine fused triazole glycoconjugates as potential SGLT2 inhibitors.
Synthesis and evaluation of l-rhamnose 1C-phosphonates as nucleotidylyltransferase inhibitors
Loranger, Matthew W.,Forget, Stephanie M.,McCormick, Nicole E.,Syvitski, Raymond T.,Jakeman, David L.
, p. 9822 - 9833 (2013/10/22)
We report the synthesis of a series of phosphonates and ketosephosphonates possessing an l-rhamnose scaffold with varying degrees of fluorination. These compounds were evaluated as potential inhibitors of α-d-glucose 1-phosphate thymidylyltransferase (Cps2L), the first enzyme in Streptococcus pneumoniae l-rhamnose biosynthesis, and a novel antibiotic target. Enzyme-substrate and enzyme-inhibitor binding experiments were performed using water-ligand observed binding via gradient spectroscopy (WaterLOGSY) NMR for known sugar nucleotide substrates and selected phosphonate analogues. IC 50 values were measured and Ki values were calculated for inhibitors. New insights were gained into the binding promiscuity of enzymes within the prokaryotic l-rhamnose biosynthetic pathway (Cps2L, RmlB-D) and into the mechanism of inhibition for the most potent inhibitor in the series, l-rhamnose 1C-phosphonate.
Synthesis of protected sugar-amino acid hybrid molecules as platform for further derivatization
Liu, Han,Li, Xuechen
supporting information, p. 6957 - 6960 (2013/01/15)
The sugar-amino acid hybrid molecules with appropriate protecting groups were synthesized from sugar-derived lactones and ester of amino acids in five high yielding steps. The C-5 of the resultant hybrid molecule, upon selective deprotection, can be further derivatized to afford the linear depsipeptide.
Efficient synthesis of carbohydrate thionolactones
Chayajarus, Kampanart,Fairbanks, Antony J.
, p. 3517 - 3520 (2007/10/03)
Carbohydrate thionolactones may be efficiently synthesized from the corresponding 1-thio sugars via a two-step procedure involving formation of a glycosyl phenylthiosulfinate by treatment with either phenylsulfinyl chloride or 1-(phenylsulfinyl)piperidine
A new Co(0) complex mediated synthesis of C-glycoside analogues
Orsini, Fulvia,Di Teodoro, Emanuela
, p. 2521 - 2528 (2007/10/03)
Properly protected glyconolactones, readily available from the parent sugars, react under mild conditions with α-bromoacetates in the presence of a soluble Co(0) complex, either in stoichiometric or substoichiometric amounts, to give a Reformatsky-type addition product to the lactone. The addition product can be subsequently converted into a variety of compounds: dehydroxylation with triethylsilane in the presence of boron trifluoride affords C-glycosides.
New stereoselective synthesis of phosphono analogues of glycosyl phosphates
Orsini,Di Teodoro
, p. 1307 - 1313 (2007/10/03)
A new and stereoselective synthesis of isosteric phosphono analogues of glycosyl phosphates is reported. Appropriately protected glyconolactones, easily available from the parent sugars are reacted with ethyl-α-iodomethylphosphonate in THF in the presence of a soluble low-valent cobalt-phosphine complex, either in stoichiometric or sub-stoichiometric amounts, in the latter case in the presence of magnesium metal. The use of magnesium metal alone works, but in a less efficient and predictable way. The intermediate addition product can be subsequently deoxygenated with triethylsilane in the presence of boron trifluoride.
SmI2-mediated reactions of diethyl iodomethylphosphonate with esters and lactones: A highly stereoselective synthesis of a precursor of the C-glycosyl analogue of thymidine 5′-(β-L-rhamnosyl)diphosphate
Orsini, Fulvia,Caselli, Alessandro
, p. 7259 - 7261 (2007/10/03)
In the presence of samarium iodide diethyl iodomethylphosphonate reacts with esters to afford β-ketophosphonates. The protocol has been applied to sugar lactones to afford in fairly good yields intermediates that are useful precursors for a variety of potentially bioactive compounds, such as the C-glycosyl analogue of thymidine 5′-(β-L-rhamnosyl)diphosphate.
Synthesis and structure of 4-O,6-O-glycosylidene glycosides
Ohtake,Ichiba,Shiro,Ikegami
, p. 8164 - 8170 (2007/10/03)
Interglycosidic spiro ortho esters (9-20) were efficiently prepared from methyl 2,6-di-O-benzylglucoor galactopyranoside and various sugar lactones in the presence of methoxytrimethylsilane and a catalytic amount of trimethylsilyl triflate. All of the prepared sugar ortho esters possess perhydrospiro[2H-pyran-2,2'-pyrano[3;2-d] [1,3]dioxin] ring systems commonly in their molecules and, remarkably, were afforded as single isomers. The configurations of the spiro centers in their molecules were determined or estimated by X-ray single crystallographic analysis and molecular modeling studies. By comparing the conformations of prepared ortho esters, we revealed that the difference in the stability between two possible isomers was principally caused from that between the spiro ring systems in their molecules in each case.
A concise and stereoselective synthesis of C-glycosyl analogues of β-L-fucopyranosyl phosphate and β-L-rhamnopyranosyl phosphate
Norris, Andrew J.,Toyokuni, Tatsushi
, p. 1097 - 1105 (2007/10/03)
The isosteric C-glycosyl analogues of β-L-fucopyranosyl phosphate 1 and β-L-rhamnopyranosyl phosphate 2 have been stereoselectively synthesized from the corresponding glycono-1,5-lactones 3 and 10 via methylphosphonylation, dehydration and catalytic hydro
