(2S)-(+)-N-methoxy-N-methyl-2,3-dimethyl-2-triethylsilyloxybutyramide | 344798-30-7

• 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: (2S)-(+)-N-methoxy-N-methyl-2,3-dimethyl-2-triethylsilyloxybutyramide
• 英文别名: (2S)-N-Methoxy-N,2,3-trimethyl-2-[(triethylsilyl)oxy]butanamide；(2S)-N-methoxy-N,2,3-trimethyl-2-triethylsilyloxybutanamide
• CAS: 344798-30-7
• 化学式: C₁₄H₃₁NO₃Si
• 分子量: 289.491
• InChiKey: VQZUIQFTCZUFSD-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.44
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S)-(+)-N-methoxy-N-methyl-2,3-dimethyl-2-triethylsilyloxybutyramide 在 正丁基锂 、 9-乙酰基蒽 、 四丁基氟化铵 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 甲苯 为溶剂， 反应 10.41h， 生成 24(S)-hydroxyvitamin D2
  参考文献：
  名称：

  A Stereospecific Synthesis of 24(S)-Hydroxyvitamin D₂, a Prodrug for 1α,24(S)-Dihydroxyvitamin D₂

  摘要：

  This contribution describes the first stereospecific synthesis of 24(S)-hydroxyvitamin D-2 (1), a metabolite of vitamin D-2. This metabolite acts as a prodrug for 1alpha,24 (S)-dihydroxy vitamin D-2 (2). which is under development for treatment of various diseases characterized by cellular hyperproliferation. The key step of the synthesis involves the Wittig-Horner olefination of (S)-2,3-dimethyl-2-triethysilyloxybutyraldehyde (17) and a vitamin D2 phosphine oxide derivative (22). The synthesis of the requisite aldehyde started with the commercially available L-(+)-valine and was completed in seven steps. The vitamin D-2 phosphine oxide derivative was synthesized in seven steps starting from vitamin D-2.

  DOI：

  10.1021/op010229e
• 作为产物：
  描述：

  (S)-(+)-2-hydroxy-2,3-dimethylbutanoic acid 在 咪唑 、 N,N'-羰基二咪唑 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2S)-(+)-N-methoxy-N-methyl-2,3-dimethyl-2-triethylsilyloxybutyramide
  参考文献：
  名称：

  A Stereospecific Synthesis of 24(S)-Hydroxyvitamin D₂, a Prodrug for 1α,24(S)-Dihydroxyvitamin D₂

  摘要：

  This contribution describes the first stereospecific synthesis of 24(S)-hydroxyvitamin D-2 (1), a metabolite of vitamin D-2. This metabolite acts as a prodrug for 1alpha,24 (S)-dihydroxy vitamin D-2 (2). which is under development for treatment of various diseases characterized by cellular hyperproliferation. The key step of the synthesis involves the Wittig-Horner olefination of (S)-2,3-dimethyl-2-triethysilyloxybutyraldehyde (17) and a vitamin D2 phosphine oxide derivative (22). The synthesis of the requisite aldehyde started with the commercially available L-(+)-valine and was completed in seven steps. The vitamin D-2 phosphine oxide derivative was synthesized in seven steps starting from vitamin D-2.

  DOI：

  10.1021/op010229e

文献信息

• Method for making 24(S)-hydroxyvitamin D2
  申请人：Bone Care International, Inc.

  公开号：US06359012B1

  公开（公告）日：2002-03-19

  The invention provides a method for making 24(S)-hydroxyvitamin D2 which is a stereospecific synthesis.

  这项发明提供了一种制备24(S)-羟基维生素D2的方法，这是一种立体特异性合成。
• A Stereospecific Synthesis of 24(<i>S</i>)-Hydroxyvitamin D₂, a Prodrug for 1α,24(<i>S</i>)-Dihydroxyvitamin D₂
  作者：Lisa D. Coutts、William B. Geiss、Brian T. Gregg、Mark A. Helle、Chi-Hsin R. King、Zinovy Itov、Mary E. Mateo、Harold Meckler、Mark W. Zettler、Joyce C. Knutson

  DOI：10.1021/op010229e

  日期：2002.5.1

  This contribution describes the first stereospecific synthesis of 24(S)-hydroxyvitamin D-2 (1), a metabolite of vitamin D-2. This metabolite acts as a prodrug for 1alpha,24 (S)-dihydroxy vitamin D-2 (2). which is under development for treatment of various diseases characterized by cellular hyperproliferation. The key step of the synthesis involves the Wittig-Horner olefination of (S)-2,3-dimethyl-2-triethysilyloxybutyraldehyde (17) and a vitamin D2 phosphine oxide derivative (22). The synthesis of the requisite aldehyde started with the commercially available L-(+)-valine and was completed in seven steps. The vitamin D-2 phosphine oxide derivative was synthesized in seven steps starting from vitamin D-2.