104549-95-3Relevant academic research and scientific papers
The α-hydroxyphosphonate-phosphate rearrangement of a noncyclic substrate-some new observations
Prechelmacher, Susanne,Mereiter, Kurt,Hammerschmidt, Friedrich
, p. 3672 - 3680 (2018)
Racemic ethyl hydrogen (1-hydroxy-2-methylsulfanyl-1-phenylethyl)phosphonate was resolved with (R)-1-phenylethylamine. The (R)-configuration of the (-)-enantiomer was determined by chemical correlation. Esterification of the (-)-enantiomer with a substituted diazomethane derived from 3-hydroxy-1,3,5(10)-estratrien-17-one delivered two epimeric phosphonates separated by HPLC. Methylation with methyl fluorosulfate at the sulfur atom and treatment with a strong base induced an α-hydroxyphosphonate-phosphate rearrangement with formation of dimethyl sulphide and two enantiomerically pure enol phosphates. Their oily nature interfered with a single crystal X-ray structure analysis to determine the stereochemistry at the phosphorus atom.
Stereochemistry of the Phosphate-Phosphonate Rearrangement
Hammerschmidt, Friedrich,Voellenkle, Horst
, p. 2053 - 2064 (2007/10/02)
The enantiomerically pure 1-phenylethanols (R)-(+)-5 and (S)-(-)-5 were transformed into the diethyl phpsphates (R)-(+)-6 and (S)-(-)-6, which were subjected a phosphate-phosphonate rearrangement to give the 1-hydroxyphosphonates (-)-7 and (+)-7, respecti
