(2S,4S)-1,2:4,5-bis(3,3-pentylidenedioxy)-3-pentanone | 506418-13-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,4S)-1,2:4,5-bis(3,3-pentylidenedioxy)-3-pentanone
• 英文别名: bis[(4S)-2,2-diethyl-1,3-dioxolan-4-yl]methanone
• CAS: 506418-13-9
• 化学式: C₁₅H₂₆O₅
• 分子量: 286.368
• InChiKey: YLQSGULOWRCXKG-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,4S)-1,2:4,5-bis(3,3-pentylidenedioxy)-3-pentanone 在 camphor-10-sulfonic acid 、 水 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 49.0h， 生成 (5R)-4-[(1R)-1,2-(dihydroxy)ethyl]-5-hydroxymethylfuran-2-(5H)-one
  参考文献：
  名称：

  Efficient Desymmetrization of “Pseudo”-C₂-Symmetric Substrates:  Illustration in the Synthesis of a Disubstituted Butenolide from Arabitol

  摘要：

  A short synthesis of the homochiral disubstituted butenolide 1 is described in four steps from arabitol. The key steps are the selective kinetic protection of arabitol and the cyclization of 11 to form the butenolide ring. This last transformation represents a rare example of a fully stereoselective cyclitive desymmetrization process of a "pseudo"-C-2-symmetric substrate.

  DOI：

  10.1021/jo026696r
• 作为产物：
  描述：

  L-(-)-arabitol 在 pyridine-SO3 complex 、 camphor-10-sulfonic acid 、 N,N-二异丙基乙胺 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2S,4S)-1,2:4,5-bis(3,3-pentylidenedioxy)-3-pentanone
  参考文献：
  名称：

  Total Synthesis of Proposed Amphidinolide A via a Highly Selective Ring-Closing Metathesis

  摘要：

  [GRAPHIC]A highly convergent synthesis of the proposed structure of amphidinolide A is reported. Instructive applications of several organometallic processes are illustrated, including a highly selective ring-closing metathesis reaction.

  DOI：

  10.1021/ol0262284

文献信息

• WO2006/89942
  申请人：——

  公开号：——

  公开（公告）日：——
• Total Synthesis of Proposed Amphidinolide A via a Highly Selective Ring-Closing Metathesis
  作者：Robert E. Maleczka,、Lamont R. Terrell、Feng Geng、Joseph S. Ward

  DOI：10.1021/ol0262284

  日期：2002.8.1

  [GRAPHIC]A highly convergent synthesis of the proposed structure of amphidinolide A is reported. Instructive applications of several organometallic processes are illustrated, including a highly selective ring-closing metathesis reaction.
• Protease inhibitor precursor synthesis
  申请人：Linclau Bruno

  公开号：US20090054668A1

  公开（公告）日：2009-02-26

  The present invention provides a compound having the structure (I) and processes for the production thereof and the intermediates used in such process.
• PROTEASE INHIBITOR PRECURSOR SYNTHESIS
  申请人：LINCLAU Bruno

  公开号：US20120041215A1

  公开（公告）日：2012-02-16

  The present invention provides a compound having the structure (I) and processes for the production thereof and the intermediates used in such process.
• US8067463B2
  申请人：——

  公开号：US8067463B2

  公开（公告）日：2011-11-29