methyl 1α,3α-dihydroxy-2β-methoxy-27-nor-cholest-5-en-26-oate | 184360-08-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: methyl 1α,3α-dihydroxy-2β-methoxy-27-nor-cholest-5-en-26-oate
• CAS: 184360-08-5
• 化学式: C₂₈H₄₆O₅
• 分子量: 462.67
• InChiKey: JSKZXWIYMNNYNT-HMKLLKBZSA-N

反应信息

• 作为反应物：
  描述：

  methyl 1α,3α-dihydroxy-2β-methoxy-27-nor-cholest-5-en-26-oate 在 3,5-二甲基吡唑 、 chromium(VI) oxide 、 4-二甲氨基吡啶 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 methyl 1α,3α-diacetoxy-2β-methoxy-7-oxo-27-nor-cholest-5-en-26-oate
  参考文献：
  名称：

  Synthesis and biological activities of 26-hydroxy-27-nor-derivatives of 1α,25-dihydroxyvitamin D3

  摘要：

  Starting with (20S)-20-(p-toluenesulfonyl)oxymethyl-pregna-1,5-dien-3 alpha-ol (4), we synthesized three vitamin D analogs in 10 to 11 steps: 1 alpha,26-dihydroxy-27-nor-vitamin D-3 (1), its 3-epi analog (2), and 2 beta-methoxy-1 alpha,26-dihydroxy-27-nor-vitamin D-3 (3). We tested the derivatives in the murine mesenchymal cell line C3H10T1/2. All substances were less potent in inhibition of cell proliferation, inhibition of adipocyte differentiation, and induction of gene activation, and had a lower affinity to the vitamin D receptor than the native vitamin D-3 metabolite 1,25(OH)(2)D-3. The affinity of 1 to the vitamin D binding protein was about three limes higher than that of 1,25(OH)(2)D-3. (C) 1996 by Elsevier Science Inc.

  DOI：

  10.1016/s0039-128x(96)00120-1
• 作为产物：
  描述：

  重氮甲烷 、 (R)-6-((1R,2R,3S,8S,9S,10R,13R,14S,17R)-1,3-Dihydroxy-2-methoxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-heptanoic acid 以 甲醇 、 乙醚 为溶剂， 反应 5.0h， 以0.66 g的产率得到methyl 1α,3α-dihydroxy-2β-methoxy-27-nor-cholest-5-en-26-oate
  参考文献：
  名称：

  Synthesis and biological activities of 26-hydroxy-27-nor-derivatives of 1α,25-dihydroxyvitamin D3

  摘要：

  Starting with (20S)-20-(p-toluenesulfonyl)oxymethyl-pregna-1,5-dien-3 alpha-ol (4), we synthesized three vitamin D analogs in 10 to 11 steps: 1 alpha,26-dihydroxy-27-nor-vitamin D-3 (1), its 3-epi analog (2), and 2 beta-methoxy-1 alpha,26-dihydroxy-27-nor-vitamin D-3 (3). We tested the derivatives in the murine mesenchymal cell line C3H10T1/2. All substances were less potent in inhibition of cell proliferation, inhibition of adipocyte differentiation, and induction of gene activation, and had a lower affinity to the vitamin D receptor than the native vitamin D-3 metabolite 1,25(OH)(2)D-3. The affinity of 1 to the vitamin D binding protein was about three limes higher than that of 1,25(OH)(2)D-3. (C) 1996 by Elsevier Science Inc.

  DOI：

  10.1016/s0039-128x(96)00120-1