Cyclobutane-Containing Scaffolds as Useful Intermediates in the Stereoselective Synthesis of Suitable Candidates for Biomedical Purposes: Surfactants, Gelators and Metal Cation Ligands
Abstract
:1. Introduction
2. Results and Discussion
2.1. Amphiphiles from 1,2-Disubstituted Cyclobutane Scaffolds: Surfactants and LMWG
2.2. Highly Rigid Polydentate Ligands From 1,3-disubstituted Cyclobutane Scaffolds
3. Materials and Methods
3.1. General Procedures
3.2. Experimental Section
3.2.1. Synthesis of tert-Butyl (1S,2R)-2-Hydroxymethylcyclobutane-1-Carboxylate (2)
3.2.2. Synthesis of tert-Butyl (1R,2S)-2-Tosyloxymethylcyclobutane-1-Carboxylate (3)
3.2.3. Synthesis of tert-Butyl (1S,2R)-2-Dodecanamidomethylcyclobutane-1-Carboxylate (5) through amine 4
3.2.4. Synthesis of (1S,2R)-2-Dodecanamidomethylcyclobutane-1-Carboxylic Acid (6)
3.2.5. Synthesis of tert-Butyl (1S,2R)-2-Hydroxymethylcyclobutane-1-Carbamate (8)
3.2.6. Synthesis of (1S,2R)-1-tert-Butyloxycarbonylaminocyclobutane-1-Methyl Dodecanoate (11)
3.2.7. Synthesis of (1S,2R)-2-Dodecanoyloxymethylcyclobutane-1-Ammonium Chloride (12)
3.2.8. Synthesis of tert-Butyl (1S,2R)-2-Tosyloxymethylcyclobutane-1-Carboxylate (9)
3.2.9. Synthesis of tert-Butyl (1S,2S)-2-Dodecanamidomethylcyclobutane-1-Carbamate (13) through diamine 10
3.2.10. Synthesis of (1S,2R)-2-Dodecanamidomethylcyclobutane-1-Ammonium Chloride (14)
3.2.11. Synthesis of Diamides 16 and 17. General Procedure
(1S,2S)-N-Dodecyl-2-Dodecanamidocyclobutane-1-Carboxamide (16)
(1S,2S)-N-Hexadecyl-2-Palmitamidocyclobutane-1-Carboxamide (17)
3.2.12. Synthesis of Tetra-tert-Butyl N,N,N’,N’-[((1S,3R)-2,2-Dimethylcyclobutane-1,3-diyl) Bis(Methylene)Bis(Azanetriyl)] Tetraacetate (20)
3.2.13. Synthesis of N,N,N’,N’-[((1S,3R)-2,2-dimethylcyclobutane-1,3-diyl) bis(methylene)-bis(azanetriyl)] tetraacetic acid (21)
3.2.14. Synthesis of Dimethyl 6,6′-[{2,2-Dimethylcyclobutane-1,3-diylbis[(2-tert-butoxy-2-oxoethyl)- azanemethylenediyl]}bis(methylene)] dipicolinate (24) through compound (23)
3.2.15. Synthesis of 6,6′-[{2,2-dimethylcyclobutane-1,3-diylbis[(carboxymethyl) azane methylene diyl]}- bis(methylene)] dipicolinic acid (25)
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Conflicts of Interest
Abbreviations
ATR | Attenuated Total Reflection |
CBAA | Cyclobutane Amino Acid |
DDS | Drug Delivery Systems |
DIPEA | Diisopropylethylamine |
DMAP | Dimethylaminopyridine |
DMF | Dimethylformamide |
DNA | Deoxyribonucleic Acid |
ESI | Electrospray Ionization |
HRMS | High-Resolution Mass Spectrometry |
IR | Infrared |
LMWG | Low Molecular-Weight Gelator |
MS | Mass Spectrometry |
NMR | Nuclear Magnetic Resonance |
NPY | Neuropeptide Y |
PyBOP | (Benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate |
QTOF | Quadrupole Time-of-Flight |
TEA | Triethylamine |
TFA | Trifluoroacetic Acid |
THF | Tetrahydrofuran |
TLC | Thin layer chromatography |
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Illa, O.; Serra, A.; Ardiaca, A.; Herrero, X.; Closa, G.; Ortuño, R.M. Cyclobutane-Containing Scaffolds as Useful Intermediates in the Stereoselective Synthesis of Suitable Candidates for Biomedical Purposes: Surfactants, Gelators and Metal Cation Ligands. Int. J. Mol. Sci. 2019, 20, 4333. https://doi.org/10.3390/ijms20184333
Illa O, Serra A, Ardiaca A, Herrero X, Closa G, Ortuño RM. Cyclobutane-Containing Scaffolds as Useful Intermediates in the Stereoselective Synthesis of Suitable Candidates for Biomedical Purposes: Surfactants, Gelators and Metal Cation Ligands. International Journal of Molecular Sciences. 2019; 20(18):4333. https://doi.org/10.3390/ijms20184333
Chicago/Turabian StyleIlla, Ona, Albert Serra, Agustí Ardiaca, Xavier Herrero, Guillem Closa, and Rosa M. Ortuño. 2019. "Cyclobutane-Containing Scaffolds as Useful Intermediates in the Stereoselective Synthesis of Suitable Candidates for Biomedical Purposes: Surfactants, Gelators and Metal Cation Ligands" International Journal of Molecular Sciences 20, no. 18: 4333. https://doi.org/10.3390/ijms20184333