| 19610607 |
Yamagishi T, Muronoi S, Hikishima S, Shimeno H, Soeda S, Yokomatsu T: Diastereoselective Synthesis of gamma-Amino-delta-hydroxy-alpha,alpha-difluorophosphonates: A Vehicle for Structure-activity Relationship Studies on SMA-7, a Potent Sphingomyelinase Inhibitor. J Org Chem. 2009 Jul 17.
A highly diastereoselective synthesis of 2-amino alcohol derivatives bearing a difluoromethylphosphonothioate group at the 3-position was achieved through LiAlH (O-t-Bu)(3)-mediated reduction of the corresponding alpha-amino ketones. The phosphonothioate moiety of the product was readily converted into the corresponding phosphonate by oxidation with m-CPBA, followed by aqueous workup. The developed methods should be useful for SAR studies of SMA-7, a potent inhibitor of SMases. |
31(0,1,1,1) |