211558-01-9Relevant academic research and scientific papers
2-Nitro-thioglycosides: α-and β-selective generation and their potential as β-selective glycosyl donors
Peng, Peng,Geng, Yiqun,G?ttker-Schnetmann, Inigo,Schmidt, Richard R.
, p. 1421 - 1424 (2015)
Michael-type addition of thiolates to 2-nitro-d-glucal or to 2-nitro-d-galactal derivatives readily provides 2-deoxy-2-nitro-1-thioglycosides. Kinetic and thermodynamic reaction control permitted formation of either the α-or preferentially the β-anomers,
An efficient route toward 2-amino-β-D-galacto-and -glucopyranosides via stereoselective michael-type addition of 2-nitroglycals
Xue, Weihua,Sun, Jiansong,Yu, Biao
experimental part, p. 5079 - 5082 (2009/10/17)
(Chemical Equation Presented) Under the catalysis of DMAP or PPY in CH 2Cl2, the Michael-type addition of nucleophiles to 2-nitrogalactal or 2-nitroglucal leads in excellent yields and stereoselectivity to the corresponding β-galacto
Convenient glycoside synthesis of amino sugars: Michael-type addition to 2-nitro-D-galactal
Das, Jagattaran,Schmidt, Richard R.
, p. 1609 - 1613 (2007/10/03)
Formation of 3,4,6-tri-O-benzyl-2-nitro-D-galactal (3) was readily accomplished starting from tri-O-benzyl-D-galactal (1) by acetyl nitrate addition to 2 and base-promoted acetic acid elimination. Addition of alcohols to 3 under conditions of base catalysis afforded 2-deoxy-2-nitrogalactopyranosides 4a-e in high yields; high α-selectivity was obtained with strong bases, whereas weaker bases furnished mainly the corresponding β-galactopyranosides. Chemoselective nitro group reduction in these glycosides was successfully carried out in the case of disaccharide 4cα using Raney nickel as catalyst, thereby affording after N-acetylation the corresponding 2-acetylamino-2-deoxy derivative 5cα.
