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The Facile Synthesis of a Carceplex with Four Disulfide Bridges
The Facile Synthesis of a Carceplex with Four Disulfide Bridges
Bulletin of the Korean Chemical Society. 2014. Jul, 35(7): 2205-2206
Copyright © 2014, Korea Chemical Society
  • Received : March 12, 2014
  • Accepted : March 28, 2014
  • Published : July 20, 2014
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About the Authors
Jaeyeon Shin
Kyungsoo Paek

Abstract
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Experimental
All commercial solvents and reagents were used without further purification except as noted below. THF was distilled from sodium benzophenone ketyl. Analytical thin-layer chromatography (TLC) was carried out on Merck silica gel 60F254 glass plate and column chromatography was performed on Merck silica gel 60 (70-230 mesh). 1 H-NMR spectra was obtained using a Bruker Advanced Digital 400 spectrometer. Chemical shifts are reported relative to tetramethylsilane tetramethylsilane peak. MALDI-TOF spectrum was obtained using an Applied Biosystems Voyager-DE STR biospectrometer at NCIRF (Seoul National University).
2MeOH@carceplex 3. To a stirred solution of cavitand 2 (R = heptyl, X = Br, 100 mg) and K 2 CO 3 (106 mg) in THF (1.0 mL) was added thioacetic acid (28.1 mg), and then the mixture was stirred for 2 h at rt. To the reaction mixture was added methanol (1.0 mL) and stirred for 4 h at rt. After stirring for another 24 h, the reaction mixture was neutralized by 2 mL of 1 N HCl. The mixture was partitioned with 10 mL of CH 2 Cl 2 and 10 mL of water. The organic layer was separated and dried over anhydrous MgSO 4 and the solvent was removed under reduced pressure. The product was purified by silica gel chromatography with a mixture of CH 2 Cl 2 / Hexane (1:1) as mobile phase (27 mg, 32%): MALDI-TOF MS m/z : 2304 ((carcerand 3 + 2 MeOH + Na + ), 100%); 1 H NMR (400 MHz, CDCl 3 ) δ 7.03 (s, 8H, Ar- H ), 5.86 (d, J = 7.6 Hz, 8H, outer -OC H 2 O-), 4.70 (t, J = 8.0 Hz, 8H, C H methine), 4.44 (d, J = 7.6 Hz, 8H, inner -OC H 2 O-), 4.36 (d, J = 12.4 Hz, 8H, outer -C H 2 SSC H 2 -), 3.79 (d, J = 13.2 Hz, 8H, inner -C H 2 SSC H 2 -), 2.15 (m, 16H, -C H 2 -), 1.40-1.27 (m, 80H, -(C H 2 ) 5- ), 0.88 (t, J = 6.8 Hz, 24H, -C H 3 ), -0.30 (m, 6H, encapsulated C H 3 OH).
Acknowledgements
This research was supported by Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (2012R1A1A2039112).
References
Lee M. H. , Yang Z. , Lim C. W. , Lee Y. H. , Dongbang S. , Kang C. , Kim J. S. 2013 Chem. Rev. 113 5071 -    DOI : 10.1021/cr300358b
Hayashida O. , Ichimura K. , Sato D. , Yasunaga T. 2013 J. Org. Chem. 78 5463 -    DOI : 10.1021/jo400591w
Helgeson R. C. , Hayden A. E. , Houk K. N. 2010 J. Org. Chem. 75 570 -    DOI : 10.1021/jo9012496
Sun J. , Patrick B. O. , Sherman J. C. 2009 Tetrahedron 65 7296 -    DOI : 10.1016/j.tet.2008.11.110
Han C. C. , Balakumar R. 2006 Tetrahedron Lett. 47 8255 -    DOI : 10.1016/j.tetlet.2006.09.093