342887-45-0Relevant academic research and scientific papers
Stereoselective synthesis of β-C-D-glucopyranosides using the reaction of TMSCN and Grignard reagents with cyclic five-membered sulfonium salt intermediates
Liu, Hui,Smoliakova, Irina P
, p. 2973 - 2980 (2001)
In the presence of a Lewis acid, ArSCl adducts of tri-O-benzyl-D-glucal react with vinyl ethers to form cyclic five-membered sulfonium salt intermediates. The latter are capable of reacting with TMSCN and Grignard reagents furnishing exclusively 2-S-(aryl)-2-thio-β-C-D-glucopyranosides. The one-pot reaction also proceeds with high stereoselectivity of C-C bond formation in the lateral chain providing exclusively or predominantly C-glycosides with (S)-configuration of the chiral center in the lateral chain.
