(R)-1-[(4S,5R)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]nonan-2-ol | 1383331-30-3

• 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: (R)-1-[(4S,5R)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]nonan-2-ol
• 英文别名: (2R)-1-[(4S,5R)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]nonan-2-ol
• CAS: 1383331-30-3
• 化学式: C₁₅H₃₀O₄
• 分子量: 274.401
• InChiKey: OWNZWVAYEWYXEI-HZSPNIEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-1-[(4S,5R)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]nonan-2-ol 在 2,2,6,6-四甲基哌啶氧化物 、 碘苯二乙酸 、 potassium tert-butylate 、 四丁基氟化铵 、 二异丁基氢化铝 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 25.58h， 生成 (S)-{(R)-1-[(4S,5R)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]nonan-2-yl} 3-hydroxypent-4-enoate
  参考文献：
  名称：

  The stereoselective total synthesis of (−)-achaetolide

  摘要：

  The stereoselective total synthesis of (-)-achaetolide is described in a convergent manner. Grignard addition, Wittig homologation, acetate aldol and ring closing metathesis reactions were the key steps involved. The required olefinic alcohol fragments were synthesized from a single chiral pool material 2-deoxy-D-ribose and olefinic acid fragment was prepared from acetate aldol reaction. Both the olefinic acid and alcohols were prepared in a concise method. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.03.010
• 作为产物：
  描述：

  2-deoxy-D-ribose 在 对甲苯磺酸 、 magnesium 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 19.0h， 生成 (R)-1-[(4S,5R)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]nonan-2-ol
  参考文献：
  名称：

  The stereoselective total synthesis of (−)-achaetolide

  摘要：

  The stereoselective total synthesis of (-)-achaetolide is described in a convergent manner. Grignard addition, Wittig homologation, acetate aldol and ring closing metathesis reactions were the key steps involved. The required olefinic alcohol fragments were synthesized from a single chiral pool material 2-deoxy-D-ribose and olefinic acid fragment was prepared from acetate aldol reaction. Both the olefinic acid and alcohols were prepared in a concise method. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.03.010