475107-24-5Relevant academic research and scientific papers
Oxathiaphospholane approach to the synthesis of conjugates of amino acids methyl esters with nucleosides
Baraniak, Janina,Kaczmarek, Renata,Wasilewska, Ewa,Stec, Wojciech J.
, p. 1667 - 1670 (2002)
Based upon 1,3,2-oxathiaphospholane chemistry, 5′-O-derivatization of nucleosides with the O-methyl esters of amino acids was performed and corresponding conjugates were obtained in satisfactory yield.
Oxathiaphospholane approach to N- and O-phosphorothioylation of amino acids
Baraniak, Janina,Kaczmarek, Renata,Korczynski, Dariusz,Wasilewska, Ewa
, p. 7267 - 7274 (2002)
A method of highly efficient synthesis of N- and O-phosphorothioylated amino acids was developed. N- and O-(2-Thiono-1,3,2-oxathiaphospholanyl)amino acid methyl esters (3) were prepared in high yields in reaction of amino acid methyl esters with 2-chloro-1,3,2-oxathiaphospholane in pyridine in the presence of elemental sulfur. Compounds 3 were converted in high yield into the corresponding methyl or benzyl phosphorothioamides 6 and 7 by DBU-assisted treatment with methanol or benzyl alcohol. When 3-hydroxypropionitrile was used instead of methanol or benzyl alcohol, the corresponding 2-cyanoethylphosphorothioamidates 4 were obtained in high yield, from which the 2-cyanoethyl group was removed with concentrated ammonium hydroxide. The oxathiaphospholane methodology was also applied for the phosphorylation of amino acids. Thus, 2-oxo-1,3,2-oxathiaphospholane derivatives 10 were prepared by oxidation of compounds 3 with SeO2. Compounds 10 were transformed into the corresponding phosphate diesters or amidoesters upon treatment with 3-hydroxypropionitrile in the presence of DBU. The DBU-assisted oxathiaphospholane ring-opening process in 3 and 10 did not cause any measurable C-racemization of phosphorothioylated/phosphorylated amino acids.
