195724-14-2Relevant academic research and scientific papers
From α-1,2-Anhydrosugars to C-Glycosides: The Influence of Lewis Acids and Nucleophiles on the Stereochemistry
Leeuwenburgh, Michiel A.,Van Der Marel, Gijsbert A.,Overkleeft, Herman S.,Van Boom, Jacques H.
, p. 549 - 564 (2007/10/03)
Ring opening of the epoxide function in α-1,2-anhydrosugars with alkynyl zinc and titanium compounds proceeds with retention of configuration to afford α-C-alkynylglycosides in reasonable to good yields, while the use of the corresponding alkynyltrifluoroborates results in the formation α/β mixtures. Vinyl nucleophiles predominantly afford α-products, whereas allyl and allenyl species almost exclusively yield β-C-glycosides.
Stereoselective synthesis of α-C-(alkynyl)-glycosides via ring-opening of α-1,2-anhydrosugars
Leeuwenburgh, Michiel A.,Timmers, Cornelis M.,Van Der Marel, Gijsbert A.,Van Boom, Jacques H.,Mallet, Jean-Maurice,Sinay, Pierre G.
, p. 6251 - 6254 (2007/10/03)
Ring-opening of an α-1,2-epoxide function in sugars with lithium alkynyl derivatives in the presence of zinc chloride proceeds with retention of configuration to afford n-C-(alkynyl)-glycosides in reasonable yields.
