(1S)-1-[(3R)-1,4-dioxaspiro[4.5]decan-3-yl]hexadecan-1-ol | 924888-78-8

• 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: (1S)-1-[(3R)-1,4-dioxaspiro[4.5]decan-3-yl]hexadecan-1-ol
• CAS: 924888-78-8
• 化学式: C₂₄H₄₆O₃
• 分子量: 382.627
• InChiKey: CRJRNRUZKKQKGH-XZOQPEGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  27
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S)-1-[(3R)-1,4-dioxaspiro[4.5]decan-3-yl]hexadecan-1-ol 在 咪唑 、 lithium aluminium tetrahydride 、 二苯基膦叠氮化物 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 生成 沙芬戈
  参考文献：
  名称：

  An asymmetric synthesis of (2S,3S)-safingol

  摘要：

  Two efficient asymmetric syntheses of (2S,3S)-safingol have been developed starting from easily available (R)-cyclohexy-lideneglyceraldehyde. The key steps in the syntheses were a diastereoselective addition of a suitable alkylmagnesium or lithium reagent, and simple organic transformations. Compared to earlier syntheses, the route involving alkyllithium addition is more viable practically due to its excellent diastereoselectivity, use of inexpensive materials/reagents and operational simplicity. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.11.119
• 作为产物：
  描述：

  溴代十五烷 、 (R)-1,4-二氧杂螺[4,5]癸烷-2-甲醛 在 lithium 作用下， 以 正己烷 为溶剂， 以89%的产率得到(1S)-1-[(3R)-1,4-dioxaspiro[4.5]decan-3-yl]hexadecan-1-ol
  参考文献：
  名称：

  An asymmetric synthesis of (2S,3S)-safingol

  摘要：

  Two efficient asymmetric syntheses of (2S,3S)-safingol have been developed starting from easily available (R)-cyclohexy-lideneglyceraldehyde. The key steps in the syntheses were a diastereoselective addition of a suitable alkylmagnesium or lithium reagent, and simple organic transformations. Compared to earlier syntheses, the route involving alkyllithium addition is more viable practically due to its excellent diastereoselectivity, use of inexpensive materials/reagents and operational simplicity. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.11.119

文献信息

• An asymmetric synthesis of (2S,3S)-safingol
  作者：Anubha Sharma、Sunita Gamre、Subrata Chattopadhyay

  DOI：10.1016/j.tetlet.2006.11.119

  日期：2007.1

  Two efficient asymmetric syntheses of (2S,3S)-safingol have been developed starting from easily available (R)-cyclohexy-lideneglyceraldehyde. The key steps in the syntheses were a diastereoselective addition of a suitable alkylmagnesium or lithium reagent, and simple organic transformations. Compared to earlier syntheses, the route involving alkyllithium addition is more viable practically due to its excellent diastereoselectivity, use of inexpensive materials/reagents and operational simplicity. (c) 2006 Elsevier Ltd. All rights reserved.