132125-61-2Relevant articles and documents
Addition of Dialkyl Phosphites and Dialkyl Trimethylsilyl Phosphites to 2-(Benzyloxy)propanal - Preparation of all Four Stereoisomeric (1,2-Dihydroxy-2H1>propyl)phosphonic Acids from Chiral Lactates
Hammerschmidt, Friedrich
, p. 469 - 475 (2007/10/02)
Dimethyl trimethylsilyl phosphite, diisopropyl trimethylsilyl phosphite, dimethyl phosphite, and diisopropyl phosphite were added to 2-(benzyloxy)propanals 4 and 6 at different temperatures in THF and CH2Cl2.The ratio of diastereomers formed was highest for diisopropyl trimethylsilyl phosphite (erythro/threo 3:1) and dropped to about 1:1 for diisopropy phosphite.Starting from chiral lactates all four stereoisomeric diisopropyl (2-benzyloxy-1-hydroxy-2H1>phosphonates were prepared and deprotected.The (1,2-dihydroxy-2H1>propyl)phosphonic acids formed were purified as cyclohexylammonium salts.The relative configuration of phosph onic acid of (-)-11 was determined by comparison with the salt (1R,2R)-12 derived from fosfomycin.