(-)8S,9R,13R,14S,17R,20R-(22E)-3-acetate,5(6)-22E(23)-cholestadien | 26033-11-4

• 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: (-)8S,9R,13R,14S,17R,20R-(22E)-3-acetate,5(6)-22E(23)-cholestadien
• 英文别名: (E)-22-dehydrocholest-5-en-3β-acetate；cholesta-5,22(E)-dien-3β-yl acetate；acetate of 22-dehydrocholesterol；22-Dehydrocholesterol acetate；3β-acetoxy-cholesta-5,22t-diene；3β-Acetoxy-cholesta-5,22t-dien；[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(E,2R)-6-methylhept-3-en-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 26033-11-4
• 化学式: C₂₉H₄₆O₂
• 分子量: 426.683
• InChiKey: CJUZRVVXJPNXNH-HYOPEJMISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (-)8S,9R,13R,14S,17R,20R-(22E)-3-acetate,5(6)-22E(23)-cholestadien 在 potassium carbonate 作用下， 以 甲醇 、 水 为溶剂， 生成 (3B,22E)-胆甾-5,22-二烯-3-醇
  参考文献：
  名称：

  cholesta-5，22-dien-3-beta-ol和cholesta-5,22，24-trien-3-beta-ol的侧链异构体的合成及其质量和核磁共振谱。

  摘要：

  DOI：

  10.1016/s0039-128x(70)80008-3
• 作为产物：
  描述：

  22(r)-羟基胆甾醇 在 二乙胺基三氟化硫 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 为溶剂， 反应 29.42h， 生成 (-)8S,9R,13R,14S,17R,20R-(22E)-3-acetate,5(6)-22E(23)-cholestadien
  参考文献：
  名称：

  The synthesis and biological activity of 22-fluorovitamin D3: A new vitamin D analog

  摘要：

  We synthesized 22-fluorovitamin D3 from (22S) cholest-5-ene-3 beta, 22-diol-3 beta-acetate 2. Compound 2 was treated with diethylaminosulfur trifluoride to give 22-fluorocholest-5-en-3 beta-acetate 3 and (E) 22-dehydrocholest-5-en-3 beta-acetate. Compound 3 was treated with N-bromosuccinimide to give a mixture of the respective 5,7- and 4,6-dienes. The 5,7-diene of 3 was separated from the 4,6-diene using the dienophile 4-phenyl-1,2,4-triazoline-3, 5-dione. 22-Fluoro-5 alpha,8 alpha-(3,5-dioxo-4-phenyl-1, 2,4-triazolino)-cholest-6-en-3 beta-acetate 4 was purified by flash chromatography and treated with lithium aluminum hydride to generate 22-fluorocholesta-5,7-dien-3 beta-ol 5. Photolysis of the diene 5, followed by thermal equilibration, resulted in the synthesis of 22-fluorovitamin D3 7. The vitamin 7 increased active intestinal calcium transport only at a dose of 50,000 pmol/rat, whereas vitamin D3 increased intestinal calcium transport at a dose of between 50 and 500 pmol/rat. 22-Fluorovitamin D3 7 did not mobilize bone and soft tissue calcium at a dose as high as 50,000 pmol/rat, whereas vitamin D3 was successful in doing so at a dose of 500 pmol/rat. When tested in the duodenal organ culture system, 22-fluorovitamin D3 7 had approximately 1/25th the potency of vitamin D3. It did not antagonize the activity of 1,25-dihydroxyvitamin D3. 22-Fluorovitamin D3 7 bound to the rat plasma vitamin D binding protein less avidly than vitamin D3. 22-Fluorovitamin D3 was bound very poorly to the chick intestinal cytosol receptor for 1,25-dihydroxyvitamin D3. We conclude that the introduction of fluorine at the C-22 position results in a vitamin D sterol with decreased biologic activity when compared to vitamin D3. The presence of a fluorine group at C-22 position inhibits the binding of the vitamin to rat vitamin D binding protein when compared to the binding of its hydrogen analog, vitamin D3.

  DOI：

  10.1016/0039-128x(86)90044-9

文献信息

• A convenient synthesis of the side-chain of sterols
  作者：T. Schmittberger、D. Uguen

  DOI：10.1016/0040-4039(95)02075-6

  日期：1996.1

  Potassium t-butoxide-induced Ramberg-Bäcklund rearrangement of chlorosulfones formed from a cyclopregnane-20-thiomethanol derivative has been shown to give Δ22-unsaturated steroids with high trans stereoselectivity.

  钾叔丁醇钾-诱导从cyclopregnane-20-thiomethanol衍生物形成chlorosulfones的拉姆贝格-的Backlund重排已显示给Δ 22个与高不饱和甾族化合物的反式立体选择性。
• The synthesis and the mass and nuclear magnetic resonance spectra of side chain isomers of cholesta-5,22-dien-3β-ol and cholesta-5,22,24-trien-3β-ol
  作者：Roderick F.N. Hutchins、Malcolm J. Thompson、James A. Svoboda

  DOI：10.1016/s0039-128x(70)80008-3

  日期：1970.1
• Contributions to the Study of Marine Products. XLVII 22-Dehydrocholesterol¹
  作者：WERNER BERGMANN、JOHN P. DUSZA

  DOI：10.1021/jo01103a002

  日期：1958.9
• Synthesis of sterols with modified side chains
  作者：Younus M. Sheikh、Carl Djerassi

  DOI：10.1016/0039-128x(75)90010-0

  日期：1975.7
• The synthesis and biological activity of 22-fluorovitamin D3: A new vitamin D analog
  作者：Harpal S. Gill、James M. Londowski、Robert A. Corradino、Rajiv Kumar

  DOI：10.1016/0039-128x(86)90044-9

  日期：1986.7

  We synthesized 22-fluorovitamin D3 from (22S) cholest-5-ene-3 beta, 22-diol-3 beta-acetate 2. Compound 2 was treated with diethylaminosulfur trifluoride to give 22-fluorocholest-5-en-3 beta-acetate 3 and (E) 22-dehydrocholest-5-en-3 beta-acetate. Compound 3 was treated with N-bromosuccinimide to give a mixture of the respective 5,7- and 4,6-dienes. The 5,7-diene of 3 was separated from the 4,6-diene using the dienophile 4-phenyl-1,2,4-triazoline-3, 5-dione. 22-Fluoro-5 alpha,8 alpha-(3,5-dioxo-4-phenyl-1, 2,4-triazolino)-cholest-6-en-3 beta-acetate 4 was purified by flash chromatography and treated with lithium aluminum hydride to generate 22-fluorocholesta-5,7-dien-3 beta-ol 5. Photolysis of the diene 5, followed by thermal equilibration, resulted in the synthesis of 22-fluorovitamin D3 7. The vitamin 7 increased active intestinal calcium transport only at a dose of 50,000 pmol/rat, whereas vitamin D3 increased intestinal calcium transport at a dose of between 50 and 500 pmol/rat. 22-Fluorovitamin D3 7 did not mobilize bone and soft tissue calcium at a dose as high as 50,000 pmol/rat, whereas vitamin D3 was successful in doing so at a dose of 500 pmol/rat. When tested in the duodenal organ culture system, 22-fluorovitamin D3 7 had approximately 1/25th the potency of vitamin D3. It did not antagonize the activity of 1,25-dihydroxyvitamin D3. 22-Fluorovitamin D3 7 bound to the rat plasma vitamin D binding protein less avidly than vitamin D3. 22-Fluorovitamin D3 was bound very poorly to the chick intestinal cytosol receptor for 1,25-dihydroxyvitamin D3. We conclude that the introduction of fluorine at the C-22 position results in a vitamin D sterol with decreased biologic activity when compared to vitamin D3. The presence of a fluorine group at C-22 position inhibits the binding of the vitamin to rat vitamin D binding protein when compared to the binding of its hydrogen analog, vitamin D3.