(4S,5S)-4,5-bis((R)-1-hydroxyhex-5-enyl)-2,2-dimethyl-1,3-dioxolane | 874910-10-8

• 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: (4S,5S)-4,5-bis((R)-1-hydroxyhex-5-enyl)-2,2-dimethyl-1,3-dioxolane
• 英文别名: (1R)-1-[(4S,5S)-5-[(1R)-1-hydroxyhex-5-enyl]-2,2-dimethyl-1,3-dioxolan-4-yl]hex-5-en-1-ol
• CAS: 874910-10-8
• 化学式: C₁₇H₃₀O₄
• 分子量: 298.423
• InChiKey: IOLHBUMMWUZIRF-WCVJEAGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 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：

  (4S,5S)-4,5-bis((R)-1-hydroxyhex-5-enyl)-2,2-dimethyl-1,3-dioxolane 在 palladium dichloride lead(IV) acetate 、 氧气 、 三氯化铁 、 sodium hydride 、 magnesium bromide 、 copper dichloride 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 12.5h， 生成 (6R,7R)-6-(benzyloxy)-7-hydroxynonan-2-one
  参考文献：
  名称：

  Asymmetric synthesis of unsaturated α-benzyloxyaldehydes: an enantioselective synthesis of (+)-exo-brevicomin

  摘要：

  Enantioselective synthesis of alpha-hydroxy aldehydes with an alkene tether was accomplished front L-(+)-tartaric acid, employing stereoselective reduction of a 1,4-diketone with L-selectride as the key step. Synthetic utility of these aldehydes was demonstrated in the synthesis of pine beetle pheromone (+)-exo-brevicomin. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.10.035
• 作为产物：
  描述：

  magnesium,pent-1-ene,bromide 在 L-Selectride 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 生成 (4S,5S)-4,5-bis((R)-1-hydroxyhex-5-enyl)-2,2-dimethyl-1,3-dioxolane
  参考文献：
  名称：

  （-）-centrolobine的立体选择性形式合成

  摘要：

  利用FeCl 3介导的四氢吡喃的立体选择性形成作为关键步骤，从天然存在的1-（+）-酒石酸中实现（-）-中心罗宾的立体选择性形式合成。

  DOI：

  10.1016/j.tet.2006.11.062

文献信息

• Stereoselective formal synthesis of (−)-centrolobine
  作者：Kavirayani R. Prasad、Pazhamalai Anbarasan

  DOI：10.1016/j.tet.2006.11.062

  日期：2007.1

  Stereoselective formal synthesis of (−)-centrolobine was achieved from naturally occurring l-(+)-tartaric acid, employing a facile FeCl3 mediated stereoselective formation of a tetrahydropyran as the key step.

  利用FeCl 3介导的四氢吡喃的立体选择性形成作为关键步骤，从天然存在的1-（+）-酒石酸中实现（-）-中心罗宾的立体选择性形式合成。
• Asymmetric synthesis of unsaturated α-benzyloxyaldehydes: an enantioselective synthesis of (+)-exo-brevicomin
  作者：Kavirayani R. Prasad、Pazhamalai Anbarasan

  DOI：10.1016/j.tetasy.2005.10.035

  日期：2005.12

  Enantioselective synthesis of alpha-hydroxy aldehydes with an alkene tether was accomplished front L-(+)-tartaric acid, employing stereoselective reduction of a 1,4-diketone with L-selectride as the key step. Synthetic utility of these aldehydes was demonstrated in the synthesis of pine beetle pheromone (+)-exo-brevicomin. (c) 2005 Elsevier Ltd. All rights reserved.
• Enantioselective synthesis of α-benzyloxy-ω-alkenals: application to the synthesis of (+)-exo-brevicomin, (+)-iso-exo-brevicomin, and (−)-isolaurepan
  作者：Kavirayani R. Prasad、Pazhamalai Anbarasan

  DOI：10.1016/j.tetasy.2007.05.014

  日期：2007.7

  The enantioselective synthesis of alpha-benzyloxy aldehydes containing a terminal alkene was carried out from chiral Pool L-(+)tartaric acid by employing the stereoselective reduction of a 1,4-diketone as the key step. The synthetic utility of these aldehydes was demonstrated in the synthesis of pine beetle pheromones (+)-exo-brevicomin, (+)-iso-exo-brevicomin and a formal synthesis of 2,7cis-disubstituted oxepane (-)-isolaurepan. (c) 2007 Elsevier Ltd. All rights reserved.