Improved and efficient synthesis of 1α-hydroxy-[6-2H] and 1α-hydroxy- [6,19,19-2H]vitamin D3 derivatives

Steroids

Volumn 64, Issue 6, 1999, Pages 396-403

  Iwasaki, Hiroshi ^a   Hosotani, Ryuzo ^a   Nakano, Yoshio ^a   Konno, Katsuhiro ^b   Takayama, Hiroaki ^b  

^a NOF Corporation   (Japan)

^b TEIKYO UNIVERSITY   (Japan)

Author keywords

1 Hydroxyvitamin D3 derivatives; 6 Monodeuterated product; Deuteration at the 6,19,19 positions; H D exchange reaction; Sulfur dioxide adduct

Indexed keywords

COLECALCIFEROL DERIVATIVE;

ARTICLE; CATALYSIS; DRUG STRUCTURE; DRUG SYNTHESIS; ISOMERISM; REACTION ANALYSIS;

DEUTERIUM; HYDROXYCHOLECALCIFEROLS; ISOMERISM; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; MOLECULAR STRUCTURE;

EID: 0032778385     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0039-128X(98)00117-2     Document Type: Article

References (30)

1. Bouillon R., Okamura W.H., Norman A.W. Structure-function relationships in the vitamin D endocrine system. Endocrinol Rev. 16:1995;200-257.
2. Zhu G.D., Okamura W.H. Synthesis of vitamin D (calciferol). Chem Rev. 95:1995;1877-1952.
3. Ettinger R.A., DeLuca H.F. The vitamin D endocrine system and its therapeutic potential. Adv Drug Res. 28:1996;269-312.
4. Okamura W.H., Zhu G.D. Chemistry and design structural biology of vitamin D action . Feldman D., Glorieux F.H., Pike J.W. Vitamin D. 1997;939-971 Academic Press, New York.
5. 3 with high specific activity its use in receptor studies . Biochemistry. 19:1980;2515-2521.
6. Colwell R.D., Trafford D.J.H., Varley M.J., Kirk D.N., Makin H.L.J. Stable isotope-labeled vitamin D, metabolites and chemical analogs Spectrometric studies . Steroids. 55:1990;418-432.
7. 3 in the rat. J Biol Chem. 251:1976;1020-1024.
8. 3 . Biochem Biophys Res Commun. 97:1980;1031-1037.
9. Paaren H.E., Fivizzani M.A., Schnoes H.K., DeLuca H.F. Preparation of tritium- or deuterium-labeled vitamin D analogs by a convenient general method. Proc Natl Acad Sci USA. 78:1981;6173-6175.
10. 3 via its sulfur-dioxide adducts. Tetrahedron Lett. 22:1981;3085-3088.
11. 3. Helv Chim Acta. 62:1979;1763-1769.
12. 3. Steroids. 54:1989;145-157.
13. 3 as internal standard. Steroids. 59:1994;559-563.
14. 3. Steroids. 57:1992;142-146.
15. Andrews D.A., Barton D.H.R., Cheng K.P., et al. A direct, regio- and stereoselective 1α-hydroxylation of (5E)-calciferol derivatives. J Org Chem. 51:1986;1635-1637.
16. 3. Chem Pharm Bull. 27:1979;3196-3198.
17. 3. Chem Pharm Bull. 40:1992;1120-1124.
18. 3. Chem Pharm Bull. 40:1995;189-192.
19. 3 in the chick using a new method for assessing intestinal calcium uptake. Arch Biochem Biophy. 215:1982;582-588.
20. 3-26,23-lactone in inducing differentiation of human myeloid leukemia cells. Arch Biochem Biophy. 220:1983;90-94.
21. Miyamoto Y., Shinki T., Ohyama Y., et al. Regulation of vitamin D-responsive gene expression by fluorinated analogs of calcitriol in rat osteoblastic ROS-C26 cells. J Biochem. 118:1995;1068-1076.
22. Shiuey S.-J., Partridge J.J., Uskokovic M.R. Triply convergent synthesis of 1α,25-dihydroxy-24(R)-fluorocholecalciferol. J Org Chem. 53:1988;1040-1046.
23. 3 . J Med Chem. 33:1990;480-490.
24. 2 and its 24-epimer, and determination of the C-24 configuration. Chem Pharm Bull. 40:1992;2932-2936.
25. 3. Calcif Tissue Int. 53:1993;318-323.
26. 3 by means of radical deoxygenation of alcohols. Chem Pharm Bull. 44:1996;62-66.
27. 3. Synthesis and preliminary biological evaluation. J Med Chem. 41:1998;3008-3014.
28. 3. Chem Pharm Bull. 46:1998;1932-1935.
29. 3. Tetrahedron. 54:1998;14705-14724.
30. 3. J Biol Chem. 272:1997;14115-14119.