(2S,5S)-2-(tert-butyl)-5-methyl-5-isopropyl-1,3-dioxolan-4-one | 344798-28-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧戊环
• 英文名称: (2S,5S)-2-(tert-butyl)-5-methyl-5-isopropyl-1,3-dioxolan-4-one
• 英文别名: (2S,5S)-2-tert-butyl-5-methyl-5-propan-2-yl-1,3-dioxolan-4-one
• CAS: 344798-28-3
• 化学式: C₁₁H₂₀O₃
• 分子量: 200.278
• InChiKey: ZVXBMXHTGFYNSO-KOLCDFICSA-N

物化性质

• 沸点：
  252.2±15.0 °C(Predicted)
• 密度：
  0.981±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 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：

  (2S,5S)-2-(tert-butyl)-5-methyl-5-isopropyl-1,3-dioxolan-4-one 在 氢氧化钾 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 0.5h， 以94%的产率得到(S)-(+)-2-hydroxy-2,3-dimethylbutanoic acid
  参考文献：
  名称：

  Method for making 24(S)-hydroxyvitamin D2

  摘要：

  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。

  公开号：

  US06359012B1
• 作为产物：
  描述：

  L-缬氨酸 在 硫酸 、 水 、 双(三甲基硅烷基)氨基钾 、 对甲苯磺酸 、 sodium nitrite 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 4.75h， 生成 (2S,5S)-2-(tert-butyl)-5-methyl-5-isopropyl-1,3-dioxolan-4-one
  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。
• METHOD FOR MAKING 24(S)-HYDROXYVITAMIN D 2
  申请人：BONE CARE INTERNATIONAL, INC.

  公开号：EP1240137A1

  公开（公告）日：2002-09-18
• [EN] METHOD FOR MAKING 24(S)-HYDROXYVITAMIN D2<br/>[FR] PROCEDE SERVANT A PREPARER 24(S)-HYDROXYVITAMINE D2
  申请人：BONE CARE INT INC

  公开号：WO2001046131A1

  公开（公告）日：2001-06-28

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