SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2012 , Vol. 32 >Issue 10: 1988 - 1992

DOI: https://doi.org/10.6023/cjoc201204015

Notes

Novel Synthesis of Paricalcitol by Chem-biotransformation

  • Wan Yang ,
  • Wen Peng ,
  • Zhang Pan ,
  • Lu Qun
Expand
  • School of Life Science and Engineering, Southwest Jiaotong University, Chengdu 610031

Received date: 2012-04-12

  Revised date: 2012-06-06

  Online published: 2012-06-19

Supported by

Project supported by the Science and Technology Support Fundation of Sichuan Province (No. 2010SZ124).

Fold

Abstract

Paricalcitol (9) was obtained from Vitamin D2 via a route of the combination of seven-step organic reaction and biotransformation. The overall yield was 3.24%, which was higher than those of the reported methods. The structures of all intermediates and product were confirmed by 1H NMR, 13C NMR and MS techniques.

Key words： vitamin D2; hydroxylation; paricalcitol

Cite this article

Wan Yang , Wen Peng , Zhang Pan , Lu Qun . Novel Synthesis of Paricalcitol by Chem-biotransformation[J]. Chinese Journal of Organic Chemistry, 2012 , 32(10) : 1988 -1992 . DOI: 10.6023/cjoc201204015

References

[1] Ebert, R.; Schutze, N.; Adamski, J.; Jakob, F. Mol. Cell Endocrinol. 2006, 248, 149.

[2] Abe, E.; Miyaura, C.; Sakagami, H.; Takeda, M.; Konno, K.; Yamazaki, T.; Yoshiki, S.; Suda, T. Proc. Natl. Acad. Sci. U. S. A. 1981, 78, 4990.

[3] Yamada, S.; Shimizu, M.; Yamamoto, K. Med. Res. Rev. 2003, 23, 89.

[4] Slatopolsky, E.; Cozzolino, M.; Lu, Y.; Finch, J.; Dusso, A.; Staniforth, M.; Wein, Y.; Webster, J. Kidney Int. 2003, 63, 2020.

[5] Yang, S.; Smith, C.; Dluca, H. F. Biochim. Biophys. Acta 1993, 1158, 279.

[6] Slatopolsky, E.; Finch, J.; Ritter, C.; Denda, M.; Morrissey, J.; Brown, A.; DeLuca, H. Am. J. Kidney Dis. 1955, 26, 852.

[7] Deluca, H. F.; Schnoes. H. K.; Perlman, K. L. US 5281731, 1994 [Chem. Abstr. 1993, 118, 124883].

[8] Deluca, H. F.; Schnoes, H. K.; Perlman, K. L. US 5086191, 1992 [Chem. Abstr. 1992, 116, 255878].

[9] Li, L.-Q.; Yue, L.-R.; Xue, J.-J.; Xie, Z.-X.; Li, Y. Chin. Sci. Bull. 2012, 57, 1.

[10] Ng, C.-S.; Wei, C.-P. US 007491712, 2009 [Chem. Abstr. 2009, 150, 260414].

[11] Bader, T.; Stutz, A.; Bichsel, H. U.; Stutz, A.; Fu, C.-C. WO 2010009879, 2010 [Chem. Abstr. 2010, 152, 19236].

[12] Perlman, K. L.; Sicinski R. R.; Schnoes, H. K.; DeLuca, H. F. Tetrahedron Lett. 1990, 31, 1823.

[13] Toyoda, A.; Nagai, H.; Yamada, T.; Moriguchi, Y.; Abe, J.; Tsuchida, T.; Nagasawa; K. Tetrahedron 2009, 65, 10002. Takeda, K.; Asou, T.; Matsuda, A.; Kimura, K.; Okamura, K.; Okamoto, R.; Sasaki, J.; Adachi, T.; Omura, S. J. Ferment. Bioeng. 1994, 78, 380.

Options
Outlines

/

〈 〉