Abstract
Addition of Dialkyl Phosphites and Dialkyl Trimethylsilyl Phosphites to 2‐(Benzyloxy)propanal – Preparation of all Four Stereoisomeric (1,2‐Dihydroxy‐[1‐2H1]propyl)phosphonic Acids from Chiral LactatesDimethyl 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 diisopropyl phosphite. Starting from chiral lactates all four stereoisomeric diisopropyl (2‐benzyloxy‐1‐hydroxy‐[1‐2H1]phosphonates were prepared and deprotected. The (1,2‐dihydroxy‐[1‐2H1]propyl)phosphonic acids formed were purified as cyclohexylammonium salts. The relative configuration of phosphonic acid of (−)‐11 was determined by comparison with the salt (1R,2R)‐12 derived from fosfomycin.
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