132281-30-2Relevant academic research and scientific papers
Synthesis of N-Substituted phosphoramidic acid esters as “reverse” fosmidomycin analogues
Adeyemi, Christiana M.,Hoppe, Heinrich C.,Isaacs, Michelle,Klein, Rosalyn,Lobb, Kevin A.,Kaye, Perry T.
, p. 2371 - 2378 (2019)
An efficient synthetic pathway to a series of novel “reverse” fosmidomycin analogues has been developed, commencing from substituted benzylamines. In these analogues, the fosmidomycin hydroxamate moiety is reversed and the tetrahedral methylene carbon adjacent to the phosphonate moiety is replaced by a nitrogen atom bearing different benzyl groups. The resulting phosphonate esters were designed as potential antimalarial “pro-drugs”.
HYDROBORATION-OXIDATION OF 1-TRIALKYLSILYL DIALKYLPHOSPHORAMIDOPROPYNES REGIOSELECTIVITY AND REACTIVITY
Kerdel, Katia,Baboulene, Michel
, p. 39 - 54 (2007/10/02)
The regioselectivity of the hydroborationof 1-trialkylsilyl dialkylphosphoramidopropynes was studied.The directive role of silicon was not always observed.In some cases inductive effects of substituents led to different and event opposite regioselectivity.We found here an interaction between boron and the phosphoryl group for the C2 addition which has not previously been observed.After oxidation, this interaction leads to byproducts.Understanding of the scope and limitations of this hydroboration-oxidation reaction enabled selective synthesis of the novel phosphorylated acids and ketones.Key words: Silylated dialkylphosphoramidopropynes; hydroboration-oxidation; regioselectivity; reactivity.
Convenient Method for Preparation of Dialkylphosphoramidopropionic Acids and Esters
Kerdel, Katia,Baboulene, Michel,Lattes, Armand
, p. 2775 - 2784 (2007/10/02)
Silylation at the alpha position of N-propargyl dialkylphosphoramidates enables preparation of dialkylphosphoramido propionic acids in 50-60percent yield after hydroboration/oxidation.Treatment with Amberlyst 15 resin in the presence of methanol leads to
