Synthesis of 1 alpha,3 beta-dihydroxy-2 beta-(3-hydroxypropoxy)-5,7-choladiene derivative and its application to the synthesis of 1 alpha,25-dihydroxy-2 beta-(3-hydroxypropoxy)vitamin D-3

被引:1
|
作者
Tachibana, Y
机构
[1] Pharmaceutical Research Center of Nisshin Flour Milling Co. Ltd., Tsurugaoka, Ooimachi, Irurna-gun
关键词
D O I
10.1246/nikkashi.1996.91
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Starting from 22-benzoyloxy-3 beta-(t-butyldimethylsilyloxy)-5 alpha,8 alpha-(4-phenyl-3,5-dioxo-1,2,4-triazolidine-1,2-diyl)-23,24-dinor-1,6-choladiene (5), the PTAD (4-phenyl-3H-1,2,4-triazole-3,5-(4H)-dione) adduct of 1 alpha,3 beta-dihydroxy-2 beta-(3-hydroxypropoxy)-23,24-dinor-5,7-choladiene derivative (3) was synthesized. The steroidal synthon (3) was converted to 1 alpha,25-dihydroxy-2 beta-(3-hydroxypropoxy)vitamin D-3 (2). Oxidation of 3 afforded the corresponding C-20 carbaldehyde (4).
引用
收藏
页码:91 / 96
页数:6
相关论文
共 50 条
  • [1] Synthetic studies of vitamin D analogs .24. Convergent synthesis of 1 alpha,25-dihydroxy-2 beta-(3-hydroxypropoxy)vitamin D-3 (ED-71)
    Hatakeyama, S
    Ikeda, T
    Maeyama, J
    Esumi, T
    Iwabuchi, Y
    Irie, H
    Kawase, A
    Kubodera, N
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1997, 7 (22) : 2871 - 2874
  • [2] Synthesis of tritiated 1α,25-dihydroxy-2β-(3-hydroxypropoxy)vitamin D3 (ED-71)1
    Chugai Pharmaceutical Co., Ltd., 1-9, Kyobashi 2-Chome, Chuo-ku, Tokyo 104-8301, Japan
    J. Label. Compd. Radiopharm., 6 (519-525):
  • [3] Total synthesis of 1α,25-dihydroxy-2β-(3-hydroxypropoxy)vitamin D3 (ED-71)
    Deng, Wutong
    Pu, Qingyin
    Gong, Yimou
    Zhou, Li
    Sun, Jian
    Wang, Chao
    TETRAHEDRON, 2020, 76 (15)
  • [4] Synthesis of putative metabolites of 1α,25-dihydroxy-2β-(3-hydroxypropoxy)vitamin D3 (ED-71)
    Ono, Yoshiyuki
    Watanabe, Hiroyoshi
    Taira, Ikuo
    Takahashi, Keisuke
    Ishihara, Jun
    Hatakeyama, Susumi
    Kubodera, Noboru
    STEROIDS, 2006, 71 (07) : 529 - 540
  • [5] SYNTHESIS OF 1α,25-DIHYDROXY-2β-(3-HYDROXYPROPOXY)VITAMIN D3 (ELDECALCITOL) AND RELATED COMPOUNDS BY THE TROST CONVERGENT METHODOLOGY
    Kubodera, Noboru
    Hatakeyama, Susumi
    HETEROCYCLES, 2009, 79 : 145 - 162
  • [6] SYNTHESIS OF 1-DEOXYELDECALCITOL, A BIOLOGICALLY INTERESTING ANALOG OF 1α,25-DIHYDROXY-2β-(3-HYDROXYPROPOXY)VITAMIN D3 (ELDECALCITOL)
    Sasaki, Hirotaka
    Eto, Kohei
    Takahashi, Keisuke
    Ishihara, Jun
    Hatakeyama, Susumi
    Kubodera, Noboru
    HETEROCYCLES, 2011, 83 (06) : 1385 - 1394
  • [7] Synthesis and evaluation of a 3-position diastereomer of 1α,25-dihydroxy-2β-(3-hydroxypropoxy)vitamin D3 (ED-71)
    Hatakeyama, Susurm
    Nagashima, Satoshi
    Imai, Naoko
    Takahashi, Keisuke
    Ishihara, Jun
    Sugita, Atsuko
    Nihei, Takeshi
    Saito, Hitoshi
    Takahashi, Fumiaki
    Kubodera, Noboru
    BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (23) : 8050 - 8056
  • [8] Process developments for the practical synthesis of eldecalcitol [1α,25-dihydroxy-2β-(3-hydroxypropoxy)vitamin D3] by linear synthesis, convergent synthesis and biomimetic synthesis
    Maeyama, Junji
    Hiyamizu, Hiroko
    Takahashi, Keisuke
    Ishihara, Jun
    Kubodera, Noboru
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 241
  • [9] REGULATORY ACTIVITIES OF 2-BETA-(3-HYDROXYPROPOXY)-1-ALPHA,25-DIHYDROXY-VITAMIN-D3, A NOVEL SYNTHETIC VITAMIN-D3 DERIVATIVE, ON CALCIUM-METABOLISM
    OKANO, T
    TSUGAWA, N
    MASUDA, S
    TAKEUCHI, A
    KOBAYASHI, T
    TAKITA, Y
    NISHII, Y
    BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1989, 163 (03) : 1444 - 1449
  • [10] Synthesis and biological evaluation of a 3-positon epimer of 1α,25-dihydroxy-2β-(3-hydroxypropoxy)vitamin D3 (ED-71)
    Hatakeyama, Susumi
    Nagashima, Satoshi
    Imai, Naoko
    Takahashi, Keisuke
    Ishihara, Jun
    Sugita, Atsuko
    Nihei, Takeshi
    Saito, Hitoshi
    Takahashi, Fumiaki
    Kubodera, Noboru
    JOURNAL OF STEROID BIOCHEMISTRY AND MOLECULAR BIOLOGY, 2007, 103 (3-5): : 222 - 226