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doi:10.1016/S0957-4166(03)00278-7 
Copyright © 2003 Elsevier Science Ltd. All rights reserved.
Stereoselective synthesis, solution structure and metal complexes of (1S,2S)-2-amino-1-hydroxyalkylphosphonic acids
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Marcin Draga, Rafal Latajkaa, Elzbieta Gumienna-Konteckab, Henryk Kozlowskib and Pawel Kafarski
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Received 17 March 2003;
Abstract
The highly stereoselective synthesis of (1S,2S)-2-amino-1-hydroxyalkylphosphonic acids was achieved by addition of dimethyl phosphite to N-protected aminoaldehydes. Relative configuration and solution conformations of (1S,2S)-2-amino-1-hydroxy-alkylphosphonic acids (in D2O) and their dimethyl esters (in CDCl3 and CD3OD) were established by means of NMR basing on the dependence between observed values of coupling constants (3JHH, 3JPC, 3JHP) and corresponding dihedral angles. Potentiometric and spectroscopic methods were used for the evaluation of the structure of the complexes of (1S,2S)-2-amino-1-hydroxy-alkylphosphonic acids with Zn(II) and Cu(II) ions in aqueous solutions.
Stereochemistry Abstracts
(1S,2S)-(2-Amino-1-hydroxy)propylphosphonic acid C3H10NO4P |
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(1S,2S)-(2-Amino-1-hydroxy-4-methyl)pentyl phosphonic acid C6H16NO4P |
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(1S,2S,3S)-(2-Amino-1-hydroxy-3-methyl)pentyl phosphonic acid C6H16NO4P |
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Article Outline
- 1. Introduction
- 2. Results and disscussion
- 2.1. Stereoselective synthesis
- 2.2. Determination of absolute configuration and conformational analysis
- 2.3. Coordination studies
- 3. Conclusions
- 4. Experimental
- 4.1. General remarks
- 4.2. General procedure for the synthesis of N-Boc-α-amino alcohols 1
- 4.3. General procedure for the synthesis of N-Boc-α-amino aldehydes 2
- 4.3.1. N-Boc-(S)-α-aminoalaninal, 2a
- 4.3.2. N-Boc-(S)-α-aminoleucinal, 2b
- 4.3.3. N-Boc-(S)-α-amino-i-leucinal, 2c
- 4.4. General procedure for the synthesis of dimethyl (1S,2S)/(1R,2S)-(2-tert-butoxycarbonyloamino-1-hydroxy)alkylphosphonates 3
- 4.4.1. Dimethyl (1S,2S)/(1R,2S)-(2-tert-butoxycarbonyloamino-1-hydroxy)propylphosphonate (80/20 mixture), 3a
- 4.4.2. Dimethyl (1S,2S)/(1R,2S)-(2-tert-butoxycarbonyloamino-1-hydroxy-4-methyl)pentylphosphonate (88/12 mixture), 3b
- 4.4.3. Dimethyl (1S,2S,3S)/(1R,2S,3S)-(2-tert-butoxycarbonyloamino-1-hydroxy-3-methyl)pentylphosphonate (83/17 mixture), 3c
- 4.5. General procedure for the synthesis of dimethyl (2-amino-1-hydroxy)alkylphosphonates hydrochlorides 4
- 4.5.1. Dimethyl (1S,2S)/(1R,2S)-(2-amino-1-hydroxy)propylphosphonate hydrochloride (81/19 mixture), 4a
- 4.5.2. Dimethyl (1S,2S)/(1R,2S)-(2-amino-1-hydroxy-4-methyl)pentylphosphonate hydrochloride (88/12 mixture), 4b
- 4.5.3. Dimethyl (1S,2S,3S)/(1R,2S,3S)-(2-amino-1-hydroxy-3-methyl)pentylphosphonate hydrochloride (83/17 mixture), 4c
- 4.6. General procedure for the synthesis of (1S,2S)-2-amino-1-hydroxyalkylphosphonates 5
- 4.6.1. (1S,2S)-(2-Amino-1-hydroxy)propyl phosphonic acid, 5a
- 4.6.2. (1S,2S)-(2-Amino-1-hydroxy-4-methyl)pentyl phosphonic acid, 5b
- 4.6.3. (1S,2S,3S)-(2-Amino-1-hydroxy-3-methyl)pentyl phosphonic acid, 5c
- 4.7. Synthesis of Boc-(S)-Phe-(S)-Ala-PO3Me2, 6
- 4.8. Derivativation of 3b with (S)-O-methylmandelic acid
- Acknowledgements
- References
