88377-41-7Relevant academic research and scientific papers
One-pot Mukaiyama type carbon-Ferrier rearrangement of glycals: Application in the synthesis of chromanone 3-C-glycosides
Dash, Ashutosh K.,Madhubabu, Tatina,Yousuf, Syed Khalid,Raina, Sushil,Mukherjee, Debaraj
, p. 1 - 8 (2017)
One-pot carbon-Ferrier rearrangement of glycals with unactivated aryl methyl ketones has been developed under mild Silyl triflate catalysis. Keto methyl group of various aryl methyl ketones without being converted into silyl enol ether could directly attack anomeric position of glycals to form keto functionalized C-glycosides in moderate to good yields with high α-selectivity. The versatility of this method has been extended to the synthesis of a small library of chromanone 3-C-glycosides.
Molybdenum-catalyzed allylic substitution in glycals: A C-C bond-forming Ferrier-type reaction
Malkov, Andrei V.,Farn, Benjamin P.,Hussain, Nigel,Kocovsky, Pavel
, p. 1735 - 1745 (2007/10/03)
The mild, Lewis-acidic complexes [Mo(CO)4Br2]2, (MeCN)2Mo(CO)3(SnCl3)Cl, and (acac)2Mo(OTf)2 have been found to catalyze the C(1)-specific C-glycosylation reaction of glycal acetates 1-3 with silyl enol ethers 4a-4c and electron-rich aromatics 5a, 5b (PhOMe, PhOH). While silyl enol ethers produce predominantly α-C-glycopyranosides (with 2 : 1 to 4 : 1 selectivity), aromatics tend to afford mainly β-C-glycopyranosides (2 : 1 to 3 : 1) in a thermodynamically controlled process.
Stereocontrolled Routes to Functionalized C-Glycopyranosides
Dawe, Robert David,Fraser-Reid, Bert
, p. 522 - 528 (2007/10/02)
4,6-O-Ethylidene-D-glucopyranose (1) reacts with an acid-washed, stabilized Wittig reagent to give the trans-oct-2-enoate 2 in excellent yield.Cyclization is effected by treatment with dilute base, and after 1 h, a 1:1 mixture of anomers exists which is the optimum concentration of the α-D form.Continuing base treatment for 5 h leads to the β-D anomer exclusively. α-D-C-Glycopyranosides can be obtained as predominant products by Lewis acid catalyzed condensation of acetylated glycals with siloxyalkenes, and anomerization to the β-D forms can be effected with potassium tert-butoxide.For a given pair of these anomers, 1H or 13C NMR pa rameters can be used for assigning configuration α or β.
