(R)-1-((4S,5S)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)pentadecan-1-ol | 929540-05-6

• 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,5S)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)pentadecan-1-ol
• 英文别名: (1R)-1-[(4S,5S)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]pentadecan-1-ol
• CAS: 929540-05-6
• 化学式: C₂₁H₄₂O₄
• 分子量: 358.562
• InChiKey: SGSYXSCMWBUZRV-AABGKKOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  25
• 可旋转键数：
  15
• 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,5S)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)pentadecan-1-ol 在 三氯化铁 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以71%的产率得到(D)-xylo-octadecane-1,2,3,4-tetrol
  参考文献：
  名称：

  Stereoselective syntheses of γ-alkyl (aryl)-α,β-dihydroxy-γ-butyrolactones and naturally occurring lipid guggultetrol

  摘要：

  gamma-Oxo-butyramides derived from tartaric acid serve as excellent precursors for the synthesis of gamma-alkyl (aryl)-alpha,beta-dihydroxy-gamma-butyrolactones and for the synthesis of tetrols containing three contiguous stereogenic centres. The methodology presented here is general for the synthesis of gamma-alkyl (aryl)-alpha,beta-dihydroxy-gamma-butyrolactones. Utility of the chiral building block was demonstrated by the synthesis of naturally occurring lipid guggultetrol. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.12.037
• 作为产物：
  描述：

  tetradecylmagnesium bromide 在 sodium tetrahydroborate 、 potassium tri-sec-butyl-borohydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 4.5h， 生成 (R)-1-((4S,5S)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)pentadecan-1-ol
  参考文献：
  名称：

  Stereoselective syntheses of γ-alkyl (aryl)-α,β-dihydroxy-γ-butyrolactones and naturally occurring lipid guggultetrol

  摘要：

  gamma-Oxo-butyramides derived from tartaric acid serve as excellent precursors for the synthesis of gamma-alkyl (aryl)-alpha,beta-dihydroxy-gamma-butyrolactones and for the synthesis of tetrols containing three contiguous stereogenic centres. The methodology presented here is general for the synthesis of gamma-alkyl (aryl)-alpha,beta-dihydroxy-gamma-butyrolactones. Utility of the chiral building block was demonstrated by the synthesis of naturally occurring lipid guggultetrol. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.12.037

文献信息

• Stereoselective syntheses of γ-alkyl (aryl)-α,β-dihydroxy-γ-butyrolactones and naturally occurring lipid guggultetrol
  作者：Kavirayani R. Prasad、Appayee Chandrakumar

  DOI：10.1016/j.tet.2006.12.037

  日期：2007.2

  gamma-Oxo-butyramides derived from tartaric acid serve as excellent precursors for the synthesis of gamma-alkyl (aryl)-alpha,beta-dihydroxy-gamma-butyrolactones and for the synthesis of tetrols containing three contiguous stereogenic centres. The methodology presented here is general for the synthesis of gamma-alkyl (aryl)-alpha,beta-dihydroxy-gamma-butyrolactones. Utility of the chiral building block was demonstrated by the synthesis of naturally occurring lipid guggultetrol. (c) 2006 Elsevier Ltd. All rights reserved.