479499-99-5Relevant academic research and scientific papers
A novel synthesis of diethyl (R)-3-(N-benzyloxyamino)-2- hydroxypropylphosphonate, a precursor to hydroxylamine antibiotics FR-33289 and FR-33699
Wroblewski, Andrzej E.,Halajewska-Wosik, Anetta
, p. 3201 - 3205 (2004)
Regioselective opening of the oxirane ring at C(3) of diethyl 2,3-epoxypropylphosphonate 6 with N- or O-benzylhydroxylamine led to 3-(N-benzyl-N-hydroxyamino)- or 3-(N-benzyloxyamino)-2- hydroxypropylphosphonates, 10 or 8. From (S)-6 (ee 94%), the phosphonate (S)-10 (ee 98%) was prepared in 80% yield. Highly enantiomerically enriched (R)- and (S)-8 (ee 97%) were obtained from (R)- and (S)-6 (ee 88% and 94%), respectively.
