125472-23-3Relevant academic research and scientific papers
Ruthenium Catalyzed Stereo/Chemo/Regioselective One-Pot Synthesis of C(2)-C(3) Unsaturated and α-d-Mannopyranosyl Sulfones
Chittela, Sravanthi,Reddy, Thurpu Raghavender,Radha Krishna, Palakodety,Kashyap, Sudhir
, p. 7108 - 7116 (2015/07/28)
An efficient and divergent approach to C(2)-C(3) unsaturated glycosyl and α-d-mannopyranosyl sulfones has been developed via ruthenium-promoted direct glycosylation, oxidation, and dihydroxylation from glycal in one-pot. The presence of stoichiometric amounts of NaIO4 and in situ generation of RuO4 from a RuCl3-NaIO4 reagent system were crucial for chemoselective oxidation of sulfide in the presence of an olefin moiety. The dual-role of ruthenium in sequential glycosylation-oxidation-dihydroxylation is amenable to a wide range of thio acceptors to access α-d-mannopyranosyl sulfones in good yields with high regioselectivity.
Addition reactions of benzenesulfinic acid with glycals and 1,2-dibromosugars
Basava, Vikram,Flores, Broc,Giovine, Matthew,Licisyn, Thomas,Walck, Katelyn,Boyko, Walter,Giuliano, Robert
experimental part, p. 389 - 400 (2009/04/11)
The addition of benzenesulfinic acid to glycals was investigated under various conditions, and optimized yields of the glycosyl phenylsulfone products were obtained in the presence of tin tetrachloride as a catalyst. Double bond shift (Ferrier rearrangement) occurred in all cases except amicetal, which lacks a substituent at the allylic carbon. Glycosylation of benzenesulfinic acid with 1,2-dibromides was carried out using silver triflate as the promoter, and gave sulfinate esters as products by reaction at oxygen rather than at sulfur. The sulfinate esters were obtained as mixtures of stereoisomers at the stereogenic sulfur atom. Trapping of the sulfinates with carboxylate nucleophiles was observed during attempted oxidation with MCPBA. Copyright Taylor & Francis Group, LLC.
Carbohydrate-derived allylic stannanes
Braithwaite, Dana H.,Holzapfel, Cedric W.,Williams, D. Bradley G.
, p. 162 - 164 (2007/10/03)
The preparation of tri(n-butyl)tin derivatives of various carbohydrates is described. Glycal derivatives were converted into the corresponding stannanes upon treatment with Bu3SnH under photochemical activation. This reaction was found to be re
SUBSTITUTION REACTIONS OF 2-BENZENESULPHONYL CYCLIC ETHERS WITH CARBON NUCLEOPHILES
Brown, Dearg S.,Bruno, Maurizio,Davenport, Raymond J.,Ley, Steven V.
, p. 4293 - 4308 (2007/10/02)
Direct substitution of 2-benzenesulphonylcyclic ethers was studied using a variety of carbon nucleophiles.These nucleophiles included organozinc reagents (derived from aryl, vinyl and alkynyl Grignard reagents) or silyl enol ethers, silyl ketene acetals,
