150993-41-2Relevant academic research and scientific papers
DAST mediated preparation of β-fluoro-α-aminophosphonates
Ka?mierczak, Marcin,Koroniak, Henryk
, p. 23 - 27 (2012)
Herein, we report a new and convenient method for the synthesis of β-fluoro-α-aminophosphonates starting from naturally occurring l-amino acids. A key step in the synthetic protocol involves nucleophilic fluorination of N,N-dibenzylated-β-amino alcohols with diethylaminosulfur trifluoride (DAST).
Regioselective Fluorination of α-Hydroxy-β-aminophosphonates by Using PyFluor
Ka?mierczak, Marcin,Kubicki, Maciej,Koroniak, Henryk
, p. 3844 - 3852 (2018/07/31)
We report a simple protocol for the synthesis of α-fluoro-β-aminophosphonates by the regioselective fluorination of α-hydroxy-β-aminophosphonates under mild conditions. The fluorination reactions were mediated by the PyFluor reagent and occurred with the retention of configuration. The main products of this reaction were a series of α-fluoro-β-aminophosphonates, which can be used as precursors in the preparation of medicinally important compounds (e.g., dipeptide analogues).
A - And B -fluorinated aminophosphonates-Synthesis and properties
Ka?mierczak, Marcin,Kubicki, Maciej,Koroniak, Henryk
, p. 459 - 468 (2016/04/09)
Interest in synthesis of fluorinated aminophosphonates has grown significantly in recent years due to their promising applications in medicinal and bioorganic chemistry. We report herein efficient and general methods for the synthesis of α- and β-monofluo
Towards convenient precursors for α-phosphonylated aziridinium ions
Piotrowska, Dorota G.,Wroblewski, Andrzej E.
experimental part, p. 998 - 1016 (2009/12/03)
Mixtures of the respective 2-(N,N-dibenzylamino)-1-chloro- and 1-(N,N-dibenzylamino)-2-chlorophosphonates were obtained after mesylation of dimethyl (1R,2S)-2-(N,N-dibenzylamino)-1-hydroxy-3-methylbutylphosphonate and diethyl (1R,2S)-2-(N,N-dibenzylamino)-1-hydroxy-3-phenylpropylphosphonate with mesyl chloride in the presence of tetraethylammonium chloride. These mixtures are considered as useful precursors to-phosphonylated aziridinium ions.
Stereodivergent synthesis of β-amino-α-hydroxyphosphonic acid derivatives by Lewis acid mediated stereoselective hydrophosphonylation of α-amino aldehydes
Yokomatsu,Yamagishi,Shibuya
, p. 1401 - 1404 (2007/10/02)
The highly diastereoselective synthesis of β-amino-α-hydroxyphosphonic acid derivatives was achieved by Lewis acid mediated hydrophosphonylation of α-dibenzylamino aldehyde. Diastereofacial differentiation could be controlled in either a chelation or a no
