141330-89-4Relevant academic research and scientific papers
Glycosylation-induced and Lewis acid-catalyzed asymmetric synthesis of β-N-glycosidically linked α-aminophosphonic acids derivatives
Wang, Yadan,Wang, Fei,Wang, Yangyun,Miao, Zhiwei,Chen, Ruyu
supporting information; experimental part, p. 2339 - 2344 (2009/10/02)
The diastereospecific formation of β-N-glycosidically linked α-aminophosphonic acids derivatives has been achieved with high yield via a Mannich-type reaction. The reaction was performed by using O-pivaloylated galactosylamine 1 as a chiral template and boron trifluoride diethyl etherate as a catalyst in THF. Imines 3 of aromatic compounds and diethyl phosphite were converted to N-galactosyl α-aminoalkylphosphonate 4, giving ratios of diastereomers higher than 19:1. This procedure provides a rapid access to biologically important galactosyl α-aminophosphonic acids derivatives.
Carbohydrates as chiral templates: Stereoselective synthesis of (R)- and (S)-α-aminophosphonic acid derivatives
Laschat,Kunz
, p. 90 - 95 (2007/10/02)
The stereoselective synthesis of diethyl (S)- or (R)-α-[(O-pivaloyl-hexapyranosyl)amino]benzylphosphonates is achieved via Lewis acid catalyzed addition of diethyl phosphite to O-pivaloylated N-benzylidene-β-D-galactosylamine or N-benzylidene-α-D-arabinop
