Convergent synthesis of 1α,25-dihydroxy-2β-(3-hydroxypropoxy)vitamin D3 (ED-71)

Bioorganic and Medicinal Chemistry Letters

Volumn 7, Issue 22, 1997, Pages 2871-2874

  Hatakeyama, Susumi ^a   Ikeda, Tatsuhiko ^a   Maeyama, Junji ^a   Esumi, Tomoyuki ^a   Iwabuchi, Yoshiharu ^a   Irie, Hiroshi ^a   Kawase, Akira ^b   Kubodera, Noboru ^b  

^a NAGASAKI UNIVERSITY   (Japan)

^b CHUGAI PHARMACEUTICAL CO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2BETA (3 HYDROXYPROPOXY)CALCITRIOL; VITAMIN D BINDING PROTEIN; VITAMIN D DERIVATIVE;

ARTICLE; BINDING AFFINITY; DRUG STRUCTURE; DRUG SYNTHESIS; OSTEOPOROSIS;

EID: 0030691215     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(97)10095-6     Document Type: Article

References (10)

1. This forms part 25 of "Synthetic Studies of Vitamin D Analogs," Part 24: Ono, Y., Watanabe, H., Shiraishi, A., Takeda, S., Higuchi, Y., Sato, K., Tsugawa, N., Okano, T., Kobayashi, T. and Kubodera, N. Chem. Pharm. Bull., in press.
2. Miyamoto, K., Murayama, E., Ochi, K., Watanabe, H. and Kubodera, N. (1993) Chem. Pharm. Bull. 41, 1111-1113.
3. Okano, T., Tsugawa, N., Masuda, S., Takeuchi, A., Kobayashi, T., Takita, Y. and Nishii, Y. (1989) Biochem. Biophys. Res. Commun. 163, 1444-1449.
4. Kobayashi, T., Okano, T., Tsugawa, N., Murano, M, Masuda, S., Takeuchi, A., Sato, K. and Nishii, Y. (1993) BioMed. Chem. Lett. 3, 1815-1819.
5. Nicolaou, K. C., Papahatjis, D. P., Claremon, D. A., Magolda, R. L. and Dolle, R. E. (1985) J. Org. Chem. 50, 1440-1456.
6. Hatakeyama, S., Irie, H., Shintani, T., Noguchi, Y., Yamada, H. and Nishizawa, M. (1994) Tetrahedron 50, 13369-13376.
7. 3) δ 5.53 (t, 1H, J=6.9Hz), 5.26 (br s, 1H), 4.85 (q, 1H, J=1.1Hz), 4.25 (d, 1H, J=6.9Hz), 4.23-4.14 (m, 3H), 3.72-3.65 (m, 3H), 3.59 (dt, 1H, J=9.4, 6.6Hz), 3.19 (dd, 1H, J=6.6, 2.0Hz), 2.42 (dd, 1H, J=13.0, 7.3Hz), 2.21 (dd, 1H, J=13.0, 3.2Hz), 1.78 (m, 2H), 0.90 (s, 9H), 0.89 (s, 9H), 0.88 (s, 9H), 0.09 (s, 3H), 0.07 (s, 3H), 0.06 (s, 3H), 0.05 (s, 3H), 0.04 (s, 6H).
8. 3) δ5.54 (tt, 1H, J=5.5, 2.1Hz), 5.35 (t, 1H, J=2.3Hz), 4.83 (t, 1H, J=2.3Hz), 4.30 (dd, 1H, J=8.0, 12.8Hz), 4.14 (qd, 1H, J=2.1, 12.8Hz), 3.97 (q, 1H, J=2.3, 4.8Hz), 3.80-3.65 (m, 5H), 3.53 (s, 1H), 2.65 (t, 1H, J=12. 1Hz), 2, 13(dd, 1H, J=4.8, 12. 1Hz), 1.78 (quint, 1H, J=6.6Hz), 0.94 (s, 9H), 0.90 (s, 9H), 0.87 (s, 9H), 0.07 (s, 6H), 0.07 (s. 6H), 0.02 (s, 6H).
9. Baggiolini, E. G., lacobelli, J. A., Hennessy, B. M., Batcho, A. D., Sereno, J. F. and Uskokovic, M. R. (1986) J. Org. Chem. 51, 3098-3108.
10. Hatakeyama, S., Sugawara, K., Numata, H. and Takano, S. (1991) J. Org. Chem. 56, 461-463.