(1S,2R,5S,6S,9R,10R,13S,15S)-13-[tert-butyl(dimethyl)silyl]oxy-5-[(1S)-1-(3-hydroxy-3-methylbutoxy)ethyl]-6,10-dimethyl-18-phenyl-16,18,20-triazahexacyclo[13.5.2.01,9.02,6.010,15.016,20]docos-21-ene-17,19-dione | 868360-73-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (1S,2R,5S,6S,9R,10R,13S,15S)-13-[tert-butyl(dimethyl)silyl]oxy-5-[(1S)-1-(3-hydroxy-3-methylbutoxy)ethyl]-6,10-dimethyl-18-phenyl-16,18,20-triazahexacyclo[13.5.2.01,9.02,6.010,15.016,20]docos-21-ene-17,19-dione
• CAS: 868360-73-0
• 化学式: C₄₀H₆₁N₃O₅Si
• 分子量: 692.027
• InChiKey: OPBQIIOGLDAUGE-LQDXTKMUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.36
• 重原子数：
  49
• 可旋转键数：
  9
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  82.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,2R,5S,6S,9R,10R,13S,15S)-13-[tert-butyl(dimethyl)silyl]oxy-5-[(1S)-1-(3-hydroxy-3-methylbutoxy)ethyl]-6,10-dimethyl-18-phenyl-16,18,20-triazahexacyclo[13.5.2.01,9.02,6.010,15.016,20]docos-21-ene-17,19-dione 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 11.0h， 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 N-溴代丁二酰亚胺(NBS) 、 9-borabicyclo[3.3.1]nonane dimer 、 cerium(III) chloride 、 偶氮二异丁腈 、 potassium tert-butylate 、 sodium hydride 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 20.25h， 生成 (1S,2R,5S,6S,9R,10R,13S,15S)-13-[tert-butyl(dimethyl)silyl]oxy-5-[(1S)-1-(3-hydroxy-3-methylbutoxy)ethyl]-6,10-dimethyl-18-phenyl-16,18,20-triazahexacyclo[13.5.2.01,9.02,6.010,15.016,20]docos-21-ene-17,19-dione
  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