141331-12-6Relevant articles and documents
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.