<(aS*,3'R,5'R)-3',5'-bis<(tert-butyldimethylsilyl)oxy>-4'-<(trimethylsilyl)oxy>cyclohexylidene>acetic acid methyl ester | 159685-66-2

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: <(aS*,3'R,5'R)-3',5'-bis<(tert-butyldimethylsilyl)oxy>-4'-<(trimethylsilyl)oxy>cyclohexylidene>acetic acid methyl ester
• 英文别名: <(aS^*,3'R,5'R)-3',5'-bis<(tert-butyldimethylsilyl)oxy>-4'-<(trimethylsilyl)oxy>cyclohexylidene>acetic acid methyl ester
• CAS: 159685-66-2
• 化学式: C₂₄H₅₀O₅Si₃
• 分子量: 502.915
• InChiKey: OGCZGQOUSBNQFP-OAFBPUBKSA-N

物化性质

• 沸点：
  454.0±45.0 °C(predicted)
• 密度：
  0.95±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.88
• 重原子数：
  32.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  <(aS*,3'R,5'R)-3',5'-bis<(tert-butyldimethylsilyl)oxy>-4'-<(trimethylsilyl)oxy>cyclohexylidene>acetic acid methyl ester 在 四氢呋喃 、 溶剂黄146 作用下， 反应 40.0h， 以83%的产率得到<(aS^*,3'R,5'R)-3',5'-bis<(tert-butyldimethylsilyl)oxy>-4'-hydroxycyclohexylidene>acetic acid methyl ester
  参考文献：
  名称：

  Synthesis and Biological Activity of 2-Hydroxy and 2-Alkoxy Analogs of 1.alpha.,25-Dihydroxy-19-norvitamin D3

  摘要：

  1 alpha,2 alpha,25 Trihydroxy-19-norvitamin D-3, 1 alpha,2 beta,25-trihydroxy-19-norvitamin D-3, and their alkoxy analogs were efficiently prepared in a convergent synthesis, starting with (-)-quinic acid and a Windaus-Grundmann type ketone. Configurations of the A-ring fragment substituents were determined by H-1,H-1 COSY 2D spectra and H-1 NOE difference spectroscopy. The new analogs exhibited selective activity in stimulating intestinal calcium transport while having little or no activity in mobilizing bone calcium. They also showed HL-60-differentiating activity equal to or 10 times lower than that of 1 alpha,25-dihydroxyvitamin D-3.

  DOI：

  10.1021/jm00048a009
• 作为产物：
  描述：

  (3R,5R)-3,5-bis[tert-butyl(dimethyl)silyloxy]-4-hydroxycyclohexanone 在 lithium diisopropyl amide 作用下， 以 二氯甲烷 为溶剂， 反应 22.25h， 生成 <(aS*,3'R,5'R)-3',5'-bis<(tert-butyldimethylsilyl)oxy>-4'-<(trimethylsilyl)oxy>cyclohexylidene>acetic acid methyl ester
  参考文献：
  名称：

  Synthesis and Biological Activity of 2-Hydroxy and 2-Alkoxy Analogs of 1.alpha.,25-Dihydroxy-19-norvitamin D3

  摘要：

  1 alpha,2 alpha,25 Trihydroxy-19-norvitamin D-3, 1 alpha,2 beta,25-trihydroxy-19-norvitamin D-3, and their alkoxy analogs were efficiently prepared in a convergent synthesis, starting with (-)-quinic acid and a Windaus-Grundmann type ketone. Configurations of the A-ring fragment substituents were determined by H-1,H-1 COSY 2D spectra and H-1 NOE difference spectroscopy. The new analogs exhibited selective activity in stimulating intestinal calcium transport while having little or no activity in mobilizing bone calcium. They also showed HL-60-differentiating activity equal to or 10 times lower than that of 1 alpha,25-dihydroxyvitamin D-3.

  DOI：

  10.1021/jm00048a009

文献信息

• Synthesis of a-ring synthon of 19-nor-1alpha,25-dihydroxyvitamin D3 from (D)-glucose
  申请人：——

  公开号：US20040133026A1

  公开（公告）日：2004-07-08

  The present invention provides a method for the synthesis of an A-ring synthon phosphine oxide used in the preparation of 19-nor vitamin D compounds, and to novel synthetic intermediates formed during the synthesis. The new method prepares the phosphine oxide from (D)-glucose.

  本发明提供了一种合成A环合成子膦氧化物的方法，该方法用于制备19-去甲维生素D化合物，并且提供了在合成过程中形成的新型合成中间体。这种新方法是从（D）-葡萄糖制备膦氧化物。