(3S,20S)-3-tert-butyldimethylsilyloxy-20-(3-oxobutoxy)pregn-5-ene | 167958-66-9

• 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: (3S,20S)-3-tert-butyldimethylsilyloxy-20-(3-oxobutoxy)pregn-5-ene
• 英文别名: 4-[(1S)-1-[(3S,8S,9S,10R,13S,14S,17S)-3-[tert-butyl(dimethyl)silyl]oxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethoxy]butan-2-one
• CAS: 167958-66-9
• 化学式: C₃₁H₅₄O₃Si
• 分子量: 502.853
• InChiKey: IEXUJUDZSQLYRA-IZPGQEACSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.34
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S,20S)-3-tert-butyldimethylsilyloxy-20-(3-oxobutoxy)pregn-5-ene 在 N-溴代丁二酰亚胺(NBS) 、 cerium(III) chloride 、 偶氮二异丁腈 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 14.25h， 生成 (3S,20S)-20-(3-hydroxy-3-methylbutoxy)pregna-5,7-dien-3-ol
  参考文献：
  名称：

  Synthesis of 1-Deoxymaxacalcitol

  摘要：

  1-Deoxymaxacalcitol, the 1-deoxygenated derivative of maxacalcitol practically used for the treatment of secondary hyperparathyroidism and psoriasis, has been synthesized for the biological evaluation. Although purification of the key intermediate containing 1,3-cyclohexadiene moiety was extremely difficult owing to inseparable contaminants, treatment of the mixture with the heterocyclic dienophile 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD) formed the readily separable Diels-Alder adduct from which the target 1-deoxymaxacalcitol could be obtained in a pure state.

  DOI：

  10.3987/com-05-10463
• 作为产物：
  描述：

  (3S)-3-tert-butyldimethylsilyloxyandrost-5-en-17-one 在 9-borabicyclo[3.3.1]nonane dimer 、 cerium(III) chloride 、 potassium tert-butylate 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 17.0h， 生成 (3S,20S)-3-tert-butyldimethylsilyloxy-20-(3-oxobutoxy)pregn-5-ene
  参考文献：
  名称：

  Synthesis of 1-Deoxymaxacalcitol

  摘要：

  1-Deoxymaxacalcitol, the 1-deoxygenated derivative of maxacalcitol practically used for the treatment of secondary hyperparathyroidism and psoriasis, has been synthesized for the biological evaluation. Although purification of the key intermediate containing 1,3-cyclohexadiene moiety was extremely difficult owing to inseparable contaminants, treatment of the mixture with the heterocyclic dienophile 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD) formed the readily separable Diels-Alder adduct from which the target 1-deoxymaxacalcitol could be obtained in a pure state.

  DOI：

  10.3987/com-05-10463

文献信息

• Synthesis of tritiated 1α,25-dihydroxy-22-oxavitamin D3
  作者：Hiroyoshi Watanabe、Masashi Akiyama、Takehiko Kawanishi、Noboru Kubodera

  DOI：10.1002/jlcr.2580360706

  日期：1995.7

  Synthesis of two tritiated 1α,25-dihydroxy-22-oxavitamin D3 (OCT), [26-3H3]OCT (3) and [2β-3H]OCT (4), is described. [26-3H3]OCT (3) was prepared by tritiation at the side chain with tritiated methylmagnesium iodide and [2β-3H]OCT (4) was labeled at the A-ring by tritiation with sodium borotritiide.

  描述了两种氚标记的1α,25-二羟基-22-氧维生素D3（OCT），即[26-3H3]OCT (3)和[2β-3H]OCT (4)的合成。[26-3H3]OCT (3)是通过用氚标记的甲基镁碘化物对侧链进行氚标记而制备的，而[2β-3H]OCT (4)则是通过与硼氚化钠进行氚标记在A环上标记的。