tert-butyl 2-[(4S)-2,4-dihydroxyoxolan-2-yl]acetate | 1067638-08-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: tert-butyl 2-[(4S)-2,4-dihydroxyoxolan-2-yl]acetate
• CAS: 1067638-08-7
• 化学式: C₁₀H₁₈O₅
• 分子量: 218.25
• InChiKey: GQHODCWBDRCPQQ-BYDSUWOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-[(4S)-2,4-dihydroxyoxolan-2-yl]acetate 、 1-萘甲酰氯 在 吡啶 作用下， 反应 1.0h， 以85%的产率得到(S)-6-(tert-butoxy)-2-hydroxy-4,6-dioxohexyl 1-naphthoate
  参考文献：
  名称：

  Efficient Synthesis of (3R,5S)-3,5,6-Trihydroxyhexanoic Acid Derivative as a Chiral Side Chain of Statins

  摘要：

  Efficient synthesis of tert-butyl [(3R,5S)-6-hydroxymeth yl-2,2-dimethyl-1,3-dioxan-4-yl]acetate (1) has been accomplished. Unprecedented hydration of 3 in the presence of lithium chloride provided 4a,b, the primary hydroxyl group of which reacted with pivaloyl-and I-naphthoyl chloride, respectively, in pyridine to give 7a or 7d in improved selectivity. Diastereoselective reduction of 7a and protection-deprotection sequence provided 1.

  DOI：

  10.1055/s-2008-1078428
• 作为产物：
  描述：

  在 水 、 对甲苯磺酸 、 lithium chloride 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以1.28 g的产率得到tert-butyl 2-[(4S)-2,4-dihydroxyoxolan-2-yl]acetate
  参考文献：
  名称：

  Efficient Synthesis of (3R,5S)-3,5,6-Trihydroxyhexanoic Acid Derivative as a Chiral Side Chain of Statins

  摘要：

  Efficient synthesis of tert-butyl [(3R,5S)-6-hydroxymeth yl-2,2-dimethyl-1,3-dioxan-4-yl]acetate (1) has been accomplished. Unprecedented hydration of 3 in the presence of lithium chloride provided 4a,b, the primary hydroxyl group of which reacted with pivaloyl-and I-naphthoyl chloride, respectively, in pyridine to give 7a or 7d in improved selectivity. Diastereoselective reduction of 7a and protection-deprotection sequence provided 1.

  DOI：

  10.1055/s-2008-1078428

文献信息

• Efficient Synthesis of (3<i>R</i>,5<i>S</i>)-3,5,6-Trihydroxyhexanoic Acid Derivative as a Chiral Side Chain of Statins
  作者：Hyunik Shin、Hyeong-wook Choi

  DOI：10.1055/s-2008-1078428

  日期：2008.6

  Efficient synthesis of tert-butyl [(3R,5S)-6-hydroxymeth yl-2,2-dimethyl-1,3-dioxan-4-yl]acetate (1) has been accomplished. Unprecedented hydration of 3 in the presence of lithium chloride provided 4a,b, the primary hydroxyl group of which reacted with pivaloyl-and I-naphthoyl chloride, respectively, in pyridine to give 7a or 7d in improved selectivity. Diastereoselective reduction of 7a and protection-deprotection sequence provided 1.