Primary hydroxy-modified cyclomaltoheptaose derivatives with two kinds of substituents. Preparation of 6I-(benzyloxycarbonylamino)-, 6I-(tert-butoxycarbonylamino)- and 6I-azido-6I-deoxy-6II,6III,6IV, 6V,6VI,6VII-hexa-O-tosylcyclomaltoheptaose and their conversion to the hexakis-(3,6-anhydro) derivatives

(Note: The full text of this document is currently only available in the PDF Version )

Hatsuo Yamamura, Tadahiro Yotsuya, Satoshi Usami, Akihito Iwasa, Shoji Ono, Yoshihisa Tanabe, Daisuke Iida, Takao Katsuhara, Kazuaki Kano, Tetsuo Uchida, Shuki Araki and Masao Kawai


Abstract

Three cyclomaltoheptaoses (1, 2 and 3) which possess a benzyloxycarbonylamino group, a tert-butoxycarbonylamino group or an azido group, and six tosyloxy groups, on their C-6 atoms have been prepared. These can be versatile intermediates for the synthesis of derivatives possessing an amino group as well as other functional groups. As an example of their derivatization, their conversion to compounds containing 3,6-anhydroglucoses, which possess cation-binding abilities, is also reported.


References

  1. Comprehensive Supramolecular Chemistry, ed. J. L. Atwood, J. E. D. Davies, D. D. MacNicol, F. Vögtle and J.-M. Lehn, Elsevier Science, Oxford, 1996, vol. 3 Search PubMed.
  2. I. Tabushi, Y. Kuroda, M. Yamada and H. Higashimura, J. Am. Chem. Soc., 1985, 107, 5545 CrossRef CAS.
  3. H. Aoyagi and M. Izumiya, Bull. Chem. Soc. Jpn., 1977, 50, 2387 CAS.
  4. H. Kappeler and R. Schwyzer, Helv. Chim. Acta, 1961, 44, 1136 CAS.
  5. T. Akiike, Y. Nagano, Y. Yamamoto, A. Nakamura, H. Ikeda, A. Ueno and F. Toda, Chem. Lett., 1994, 1089 CAS; P. R. Ashton, R. Königer, J. F. Stoddart, A. Alker and V. D. Harding, J. Org. Chem., 1996, 61, 903 CrossRef CAS.
  6. K. Hamasaki, H. Ikeda, A. Nakamura, A. Ueno, F. Toda, I. Suzuki and T. Osa, J. Am. Chem. Soc., 1993, 115, 5035 CrossRef CAS.
  7. A. R. Gibson, L. D. Melton and K. N. Slessor, Can. J. Chem., 1974, 52, 3905 CAS.
  8. C. Roehri-Stoeckel, O. Dangles and R. Brouillard, Tetrahedron Lett., 1997, 38, 1551 CrossRef CAS.
  9. (a) H. Yamamura and K. Fujita, Chem. Pharm. Bull., 1991, 39, 2505 CAS; (b) H. Yamamura, T. Kawase, M. Kawai and Y. Butsugan, Bull. Chem. Soc. Jpn., 1993, 66, 585 CAS.
  10. K. Tsujihara, H. Kurita and M. Kawazu, Bull. Chem. Soc. Jpn., 1977, 50, 1567 CAS.
  11. (a) P. R. Ashton, P. Ellwood, I. Staton and J. F. Stoddart, J. Org. Chem., 1991, 56, 7274 CrossRef CAS; (b) H. Yamamura, T. Ezuka, Y. Kawase, M. Kawai, Y. Butsugan and K. Fujita, J. Chem. Soc., Chem. Commun., 1993, 636 RSC; (c) H. Yamamura, H. Nagaoka, M. Kawai, Y. Butsugan and K. Fujita, Tetrahedron Lett., 1995, 36, 1093 CrossRef CAS; (d) H. Yamamura, H. Masuda, Y. Kawase, M. Kawai, Y. Butsugan and H. Einaga, J. Chem. Soc., Chem. Commun., 1996, 1069 RSC; (e) P. R. Ashton, G. Gattuso, R. Königer, J. F. Stoddart and D. J. Williams, J. Org. Chem., 1996, 61, 9553 CrossRef CAS.
  12. The Peptides: Analysis, Synthesis, Biology, ed. E. Gross and J. Meienhofer, Academic Press, New York, 1981, vol. 3 Search PubMed.
  13. S. Hirase and C. Araki, Bull. Chem. Soc. Jpn., 1954, 27, 105.
  14. A. Gadelle and J. Defaye, Angew. Chem., Int. Ed. Engl., 1991, 30, 78 Search PubMed; P. R. Ashton, P. Ellwood, I. Staton and J. F. Stoddart, Angew. Chem., Int. Ed. Engl., 1991, 30, 80 Search PubMed See also ref. 9 (a).
  15. F. P. Schmidtchen, Tetrahedron Lett., 1984, 25, 4361 CrossRef CAS.
Click here to see how this site uses Cookies. View our privacy policy here.