(2S,2'S,5S,5'S)-2,2'-ditertbutyl-5,5'-bis(1,3-dioxolane-4,4'-dione) | 688312-76-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S,2'S,5S,5'S)-2,2'-ditertbutyl-5,5'-bis(1,3-dioxolane-4,4'-dione)
• 英文别名: (2S,2'S,4S,4'S)-2,2'-di-tert-butyl-4,4'-bis(1,3-dioxolanyl)-5,5'-dione；(2S,5S)-2-tert-butyl-5-[(2S,4S)-2-tert-butyl-5-oxo-1,3-dioxolan-4-yl]-1,3-dioxolan-4-one
• CAS: 688312-76-7
• 化学式: C₁₄H₂₂O₆
• 分子量: 286.325
• InChiKey: DPNGDJMNARPSBR-OSTYVCCYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,2'S,5S,5'S)-2,2'-ditertbutyl-5,5'-bis(1,3-dioxolane-4,4'-dione) 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 生成 (Z)-(2S)-2-tert-butyl-5-carboxymethylene-1,3-dioxolan-4-one
  参考文献：
  名称：

  Synthesis of Z-5-Carboxymethylene-1,3-dioxolan-4-ones:  A Better Way

  摘要：

  [GRAPHICS]The title compounds were prepared by a straightforward two-step procedure. Tartaric acid was first protected as either a bis(ketal) or a bis(acetal). This intermediate was then treated with potassium tert-butoxide at reduced temperature to effect a stereoselective elimination leading to the Z diastereomer of the alpha,beta-unsaturated acid. This protocol is useful for the laboratory-scale synthesis of these compounds but can also be scaled up to produce kilogram quantities of the material.

  DOI：

  10.1021/jo0700171
• 作为产物：
  描述：

  D-酒石酸 、 特戊醛 在 lithium perchlorate 作用下， 以 乙醚 为溶剂， 反应 24.0h， 以48%的产率得到(2S,2'S,5S,5'S)-2,2'-ditertbutyl-5,5'-bis(1,3-dioxolane-4,4'-dione)
  参考文献：
  名称：

  A simple approach to 5,5′-bis(1,3-dioxolan-4-ones) of tartaric acids

  摘要：

  An easy access to acetals of aldehydes and tartaric acid is described. A series of bis(1,3-dioxolan-4-ones) was isolated with a high degree of 2,5-cis-selectivity. Transformations were performed with both (S,S)- and (R,R)-tartaric acid. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.12.016