Abstract
All possible isomers of 1,2,3-tri(N-tert-butoxycarbonylamino)propylphosphonate 6 were synthesized from the respective diethyl [N-(1-phenylethyl)]-1-benzylamino-2,3-epiiminopropylphosphonates 5 via opening the aziridine ring with trimethylsilyl azide (TMSN3) followed by hydrogenolysis in the presence of di-tert-butyl dicarbonate (Boc2O). [N-(1-phenylethyl)]-1-benzylamino-2,3-epiiminopropylphosphonates (1R,2R,1′S)-5a and (1S,2S,1′R)-5c were smoothly transformed into diethyl 3-acetoxy-1-benzylamino-2-[N-(1-phenylethyl)amino]propylphosphonates (1R,2R,1′S)-9a and (1S,2S,1′R)-9c, respectively by the opening of the aziridine ring with acetic acid. Transformations of [N-(1-phenylethyl)]-1-benzylamino-2,3-epiiminopropylphosphonates (1S,2R,1′S)-5b and (1R,2S,1′R)-5d into diethyl 3-acetoxy-1-benzylamino-2-[(1-phenylethyl)amino]propylphosphonates (1S,2R,1′S)-9b and (1R,2S,1′R)-9d were accompanied by the formation of ethyl {1-(N-benzylacetamido)-3-hydroxy-2-[(1-phenylethyl)amino]propyl}phosphonate (1S,2R,1′S)-10b and (1R,2S,1′R)-10d and 3-(N-benzylacetamido)-4-[N-(1-phenylethyl)]amino-1,2-oxaphospholane (3S,4R,1′S)-11b and (3R,4S,1′R)-11d as side products. Diethyl (1R,2R)-, (1S,2S)-, (1S,2R)- and (1R,2S)-3-acetoxy-1,2-di(N-tert-butoxycarbonylamino)propylphosphonates 7a–7d were obtained from the respective 3-acetoxy-1-benzylamino-2-[N-(1-phenylethyl)amino]propylphosphonates 9a–9d by hydrogenolysis in the presence of Boc2O.
Highlights
Aside from their fundamental role as components of proteins, amino acids are of great interest in organic synthesis since they may serve as chiral building blocks for the preparation of new pharmacologically valuable compounds, and they may be used in peptide synthesis
The 3-(N-methyl) derivative of (S)-1 [β-N-methylamino-L-alanine] is a strong neurotoxin found in the majority of cyanobacterial genera [4,5,6,7,8,9,10], while its 3-(N-oxalyl) analogue has been isolated from the grass pea, Lathyrus sativus [1,11,12]
It relies on the opening of the aziridine ring in aziridinephosphonate (1R,2R,10 S)-5a, (1S,2R,10 S)-5b, (1S,2S,10 R)-5c and
Summary
Aside from their fundamental role as components of proteins, amino acids are of great interest in organic synthesis since they may serve as chiral building blocks for the preparation of new pharmacologically valuable compounds, and they may be used in peptide synthesis. Triamino found in the structure and capreomycin type antibiotics from the marine sponge Theonella swinhoei, which acts as an inhibitor of serine proteases [13,17,18,19]. Triamino acids found in the structure of streptothricin and capreomycin type antibiotics [20,21]. The interest in the synthesis of phosphonates as occurring bioisosteres of amino acids has been growing interest in theassynthesis of phosphonates as bioisosteres of amino acids hasbeen beenidentified growing over The recent decades, many examples of biologically active compounds have. The interest in the synthesis of phosphonates as bioisosteres of amino acids has been over recent decades, as many examples of biologically active compounds have been identified [22,23].
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