3-[(4R,5R)-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl]propionic acid methyl ester | 850222-14-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3-[(4R,5R)-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl]propionic acid methyl ester
• 英文别名: methyl 3-[(4R,5R)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]propanoate
• CAS: 850222-14-9
• 化学式: C₁₀H₁₈O₅
• 分子量: 218.25
• InChiKey: VVNRKZDCUBOOBD-HTQZYQBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-[(4R,5R)-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl]propionic acid methyl ester 在 4-甲氧基-四甲基哌啶氧自由基 、 lithium hydroxide 、 sodium hypochlorite 、 2,4,6-三氯苯甲酰氯 、 四丁基氟化铵 、 双(三甲基硅烷基)氨基钾 、 碳酸氢钠 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 29.0h， 生成 8-(1-methoxymethoxyheptyl)-2,2-dimethyl-3a,4,5,8,9,11a-hexahydro-1,3,7-trioxa-cyclopentacyclodecen-6-one
  参考文献：
  名称：

  Stereoselective synthesis of microcarpalide

  摘要：

  Microcarpalide is a strong microfilament disrupting agent. The convergent and stereoselective synthesis of microcarpalide was succeeded via Julia olefination and macrolactonization. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.05.057
• 作为产物：
  描述：

  3-[(4R,5R)-5-benzyloxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl]propionic acid methyl ester 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 8.0h， 以94%的产率得到3-[(4R,5R)-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl]propionic acid methyl ester
  参考文献：
  名称：

  Stereoselective synthesis of (−)-microcarpalide

  摘要：

  A highly convergent and efficient synthesis of (-)-microcarpalide, a 10-membered lactone displaying remarkable microfilament disrupting activity is described. Ring-closing metathesis and Sharpless asymmetric dihydroxylations are the key steps. Our strategy highlights the application of novel hydroxy lactone precursors for the stereoselective synthesis of (-)-microcarpalide. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.01.052

文献信息

• Stereoselective synthesis of (−)-microcarpalide
  作者：Subhash P. Chavan、Cherukupally Praveen

  DOI：10.1016/j.tetlet.2005.01.052

  日期：2005.3

  A highly convergent and efficient synthesis of (-)-microcarpalide, a 10-membered lactone displaying remarkable microfilament disrupting activity is described. Ring-closing metathesis and Sharpless asymmetric dihydroxylations are the key steps. Our strategy highlights the application of novel hydroxy lactone precursors for the stereoselective synthesis of (-)-microcarpalide. (C) 2005 Elsevier Ltd. All rights reserved.
• Stereoselective synthesis of microcarpalide
  作者：Ken Ishigami、Hidenori Watanabe、Takeshi Kitahara

  DOI：10.1016/j.tet.2005.05.057

  日期：2005.8

  Microcarpalide is a strong microfilament disrupting agent. The convergent and stereoselective synthesis of microcarpalide was succeeded via Julia olefination and macrolactonization. (c) 2005 Elsevier Ltd. All rights reserved.