(2R,3S)-octadecane-1,2,3-triol | 924888-83-5

• 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: (2R,3S)-octadecane-1,2,3-triol
• CAS: 924888-83-5
• 化学式: C₁₈H₃₈O₃
• 分子量: 302.498
• InChiKey: NCJVFLBURTXPFQ-ZWKOTPCHSA-N

物化性质

• 沸点：
  452.1±25.0 °C(Predicted)
• 密度：
  0.948±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  21
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,3S)-octadecane-1,2,3-triol 在 palladium on activated charcoal 吡啶 、 盐酸 、 sodium azide 、 氢气 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 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：

  (R)-1,4-二氧杂螺[4,5]癸烷-2-甲醛 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 生成 (2R,3S)-octadecane-1,2,3-triol
  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.