Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Facile and Large Scale Synthesis of Diverse 4-O-Protected 2,3-O-Isopropylidene-D-erythrose

  • Received : 2010.07.01
  • Accepted : 2010.09.24
  • Published : 2010.12.20
Download PDF
⟨ Previous Next ⟩

Abstract

Keywords

References

  1. Wu, J. Z.; Gao, J.; Ren, G. B.; Zhen, Z. B.; Zhang, Y.; Wu, Y.Tetrahedron 2009, 65, 289-299. https://doi.org/10.1016/j.tet.2008.10.050
  2. Tachihara, T.; Kitahara, T.Tetrahedron 2003, 59, 1773-1780. https://doi.org/10.1016/S0040-4020(03)00119-4
  3. Kadota, K.; ElAzab, A. S.;Taniguchi, T.; Ogasawara, K. Synthesis 2000, 10, 1372-1374.
  4. Sugahara, T.; Ogasawara, K. Synlett. 1999, 4, 419-420.
  5. Pawłowska, J.; Krawczyk, K. K.; Wojtasiewicz, K.; Maurin,J. K.; Czarnocki, Z. Monatsh Chem. 2009, 140, 83-86. https://doi.org/10.1007/s00706-008-0017-2
  6. Oh, J. E.;Lee, K. H. Bioorg. Med. Chem. 1999, 7, 2985-2990. https://doi.org/10.1016/S0968-0896(99)00247-3
  7. Dickman,M.; Jones, J. B. Bioorg. Med. Chem. 2000, 8, 1957-1968. https://doi.org/10.1016/S0968-0896(00)00121-8
  8. Joshi, B. V.; Moon, H. R.; Fettinger, J. C.; Marquez, V. E.; Jacobson,K. A. J. Org. Chem. 2005, 70, 439-447. https://doi.org/10.1021/jo0487606
  9. Gallos, J. K.;Stathakis, C. I.; Kotoulas, S. S.; Koumbis, A. E. J. Org. Chem. 2005, 70, 6884-6890. https://doi.org/10.1021/jo050987t
  10. Moral, J. A.; Moon, S. J.; Torres, S. R.; Minehan, T. G. Org. Lett. 2009, 11, 3734-3737. https://doi.org/10.1021/ol901353f
  11. Bi, J.; Aggarwal, V. K. Chem. Commun.2008, 120-122.
  12. Kimura, M.; Ezoe, A.; Mori, M.; Iwata,K.; Tamaru, Y. J. Am. Chem. Soc. 2006, 128, 8559-8568. https://doi.org/10.1021/ja0608904
  13. Brabandt,W. V.; Vanwalleghem, M.; D’hooghe, M.; Kimpe, N. D. J. Org. Chem. 2006, 71, 7083-7086. https://doi.org/10.1021/jo0608319
  14. Liesener, F. P.; Jannsen, U.;Kalesse, M. Synthesis 2006, 15, 2590-2602.
  15. Curti, C.; Zanardi,F.; Battistini, L.; Sartori, A.; Rassu, G.; Auzzas, L. Roggio, A.;Pinna, L.; Casiraghi. G. J. Org. Chem. 2006, 71, 225-230. https://doi.org/10.1021/jo0520137
  16. Smith, A. B., III; Lin, Q.; Doughty, V. A.; Zhuang, L.; McBriar,M. D.; Kerns, J. K.; Boldi, A. M.; Murase, N.; Moser, W. H.; Brook,C. S.; Bennett, C. S.; Nakayama, K.; Sobukawa, M.; Trout, R. E. L.Tetrahedron 2009, 65, 6470-6488. https://doi.org/10.1016/j.tet.2009.04.001
  17. Guisot, N. A.; Lahoucine,B. O.; Canet, I.; Sinibaldi, M. E. Tetrahedron Lett. 2007, 48, 8511-8513. https://doi.org/10.1016/j.tetlet.2007.09.151
  18. Zarbin, P. H. G.; Oliveira, A. R. M.; Simonelli, F.; Villar,J. A. F. P.; Delay, O., Jr. Tetrahedron Lett. 2004, 45, 7399-7400. https://doi.org/10.1016/j.tetlet.2004.08.083
  19. Jeong, B. S.; Choi, N. S.; Ahn, S. K.; Bae, H.; Kim, H. S.; Kim,D. Bioorganic & Medicinal Chemistry Letters 2005, 15, 3580-3583. https://doi.org/10.1016/j.bmcl.2005.05.065
  20. Bennett, R. B., III; Choi, J. R.; Montgomery, W. D.; Cha,J. K. J. Am. Chem. Soc. 1989, 111, 2580-2582. https://doi.org/10.1021/ja00189a034
  21. Mondiere, A.; Peng, R.; Remuson, R.; Aitken, D. J. Tetrahedron2008, 64, 1088-1093. https://doi.org/10.1016/j.tet.2007.11.021
  22. Srihari, P.; Kumaraswamy, B.; Yadav, J. S. Tetrahedron 2009, 65,6304-6309. https://doi.org/10.1016/j.tet.2009.06.035
  23. Li, Y. L.; Drew, M. G. B.; Welchman, E. V.; Shirvastava, R. K.;Jiang, S.; Valentine, R.; Singh, G. Tetrahedron 2004, 60, 6523-6531. https://doi.org/10.1016/j.tet.2004.06.048
  24. Evans, D. A.; Glorius, F.; Burch, J. D. Org. Lett. 2005, 7, 3331-3333. https://doi.org/10.1021/ol051226f
  25. Munier, P.; Krusinski, A.; Picq, D.; Anker, D. Tetrahedron1995, 51, 1229-1244. https://doi.org/10.1016/0040-4020(94)00993-5
  26. Graham, T. J. S.; Gray, E. E.; Burgess, J. M.; Goess, B. C. J. Org. Chem. 2010, 75, 226-228. https://doi.org/10.1021/jo9020375
  27. Chen, W.; Liebeskind, L. S. J. Am. Chem. Soc. 2009, 131, 12546-12547. https://doi.org/10.1021/ja9056322
  28. Sibley, R.; Mokdad,H. H.; Schoenleber, R.; Musza, L.; Stirtan, W.; Marrero, D.; Carley,W.; Xiao, H.; Dumas, J. Bioorg. Med. Chem. Lett. 2003, 13, 1919-1922. https://doi.org/10.1016/S0960-894X(03)00307-X
  29. Munier, P.; Krusinski, A.; Picq, D.; Anker, D. Tetrahedron 1995,51, 1229-1244. https://doi.org/10.1016/0040-4020(94)00993-5
  30. Evans, D. A.; Cee, V. J.; Siska, S. J. J. Am. Chem. Soc. 2006, 128,9433-9441. https://doi.org/10.1021/ja061010o
  31. Storzl, T.; Bernet, B.; Vasella, A. Helv. Chim. Acta 1999, 82, 2380-2412. https://doi.org/10.1002/(SICI)1522-2675(19991215)82:12<2380::AID-HLCA2380>3.0.CO;2-P
  32. Kenji, O.; Hideyuki, S. Noguchi Kenkyusho Jiho 1989, 32, 39-45.

Cited by

  1. ChemInform Abstract: Facile and Large Scale Synthesis of Diverse 4-O-Protected 2,3-O-Isopropylidene-D-erythrose. vol.42, pp.18, 2011, https://doi.org/10.1002/chin.201118163
  2. Chagosensine: A Riddle Wrapped in a Mystery Inside an Enigma vol.142, pp.13, 2010, https://doi.org/10.1021/jacs.0c01700