(20R)-1α-[(tert-butyldimethylsilyl)oxy]-2-methylene-25-[(tert-butyldimethyl-silyl)oxy]-19-nor-22(E)-ene-vitamin D3 tert-butyldimethylsilyl ether | 1283571-24-3

• 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: (20R)-1α-[(tert-butyldimethylsilyl)oxy]-2-methylene-25-[(tert-butyldimethyl-silyl)oxy]-19-nor-22(E)-ene-vitamin D3 tert-butyldimethylsilyl ether
• CAS: 1283571-24-3
• 化学式: C₄₅H₈₄O₃Si₃
• 分子量: 757.417
• InChiKey: TUUPKAUIHPKVFY-UPAADYRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.57
• 重原子数：
  51.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  27.69
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (20R)-1α-[(tert-butyldimethylsilyl)oxy]-2-methylene-25-[(tert-butyldimethyl-silyl)oxy]-19-nor-22(E)-ene-vitamin D3 tert-butyldimethylsilyl ether 在 氢氟酸 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 6.0h， 以59%的产率得到(20S,22E)-2-methylene-19-nor-22-ene-1α,25-dihydroxyvitamin D3
  参考文献：
  名称：

  26-Desmethyl-2-methylene-22-ene-19-nor-1α,25-dihydroxyvitamin D3 compounds selectively active on intestine

  摘要：

  Six new analogs of 2-methylene-19-nor-1 alpha,25-dihydroxyvitamin D-3, 6-7 and 8a,b-9a,b, have been synthesized. All compounds are characterized by a trans double bond located in the side chain between C-22 and C-23. While compounds 6 and 7 possess C-26 and C-27 methyls, compounds 8a,b and 9a,b lack one of these groups. A Lythgoe-based synthesis, employing the Wittig-Horner reaction was used for these preparations. Two different types of Delta E-22-25-hydroxy Grundmann's ketone, having either only one stereogenic center located at position C-20 (20 and 21), or two stereogenic centers located at 20- and 25-positions (24a,b-25a,b) were obtained by a multi-step procedure from commercial vitamin D-2. The introduction of a double bond at C-22 appeared to lower biological activity in vitro and in vivo. Further removal of a 26-methyl in these analogs had little effect on receptor binding, HL-60 differentiation and CYP24A expression but markedly diminished or eliminated in vivo activity on bone calcium mobilization while retaining activity on intestinal calcium transport. (C) 2014 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2014.01.012
• 作为产物：
  描述：

  (8S,20S)-des-A,B-8-benzoyloxy-20-[4'-(tertbutyldimethylsilyloxy)-4'-methyl-pent-(1'E)-en-yl]-pregnane 在 重铬酸吡啶 、 4-甲基苯磺酸吡啶 、 苯基锂 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 二丁醚 为溶剂， 反应 44.5h， 生成 (20R)-1α-[(tert-butyldimethylsilyl)oxy]-2-methylene-25-[(tert-butyldimethyl-silyl)oxy]-19-nor-22(E)-ene-vitamin D3 tert-butyldimethylsilyl ether
  参考文献：
  名称：

  26-Desmethyl-2-methylene-22-ene-19-nor-1α,25-dihydroxyvitamin D3 compounds selectively active on intestine

  摘要：

  Six new analogs of 2-methylene-19-nor-1 alpha,25-dihydroxyvitamin D-3, 6-7 and 8a,b-9a,b, have been synthesized. All compounds are characterized by a trans double bond located in the side chain between C-22 and C-23. While compounds 6 and 7 possess C-26 and C-27 methyls, compounds 8a,b and 9a,b lack one of these groups. A Lythgoe-based synthesis, employing the Wittig-Horner reaction was used for these preparations. Two different types of Delta E-22-25-hydroxy Grundmann's ketone, having either only one stereogenic center located at position C-20 (20 and 21), or two stereogenic centers located at 20- and 25-positions (24a,b-25a,b) were obtained by a multi-step procedure from commercial vitamin D-2. The introduction of a double bond at C-22 appeared to lower biological activity in vitro and in vivo. Further removal of a 26-methyl in these analogs had little effect on receptor binding, HL-60 differentiation and CYP24A expression but markedly diminished or eliminated in vivo activity on bone calcium mobilization while retaining activity on intestinal calcium transport. (C) 2014 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2014.01.012