(4S,5S)-ethyl 7-(benzyloxy)-5-hydroxy-4-methylheptanoate | 1464823-38-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (4S,5S)-ethyl 7-(benzyloxy)-5-hydroxy-4-methylheptanoate
• 英文别名: ethyl (4S,5S)-5-hydroxy-4-methyl-7-phenylmethoxyheptanoate
• CAS: 1464823-38-8
• 化学式: C₁₇H₂₆O₄
• 分子量: 294.391
• InChiKey: RVAKTLSQRGOJNC-HOCLYGCPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4S,5S)-ethyl 7-(benzyloxy)-5-hydroxy-4-methylheptanoate 在 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以82%的产率得到(5S,6S)-6-(2-(benzyloxy)ethyl)-5-methyltetrahydro-2H-pyran-2-ol
  参考文献：
  名称：

  Novel iodine catalyzed diastereoselective synthesis of trans-2,6-disubstituted tetrahydro-2H-pyrans: synthesis of C1–C13 fragment of bistramide-A

  摘要：

  A new method for the stereoselective synthesis of trans 2.6-disubstituted tetrahydro-2H-pyrans has been developed involving iodine catalyzed allylation of tetrahydro-2H-pyranol with excellent trans selectivity. The method was also applied toward the construction of C1-C13 fragment of bistramide-A in 11 steps with 21.4% overall yield. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.08.085
• 作为产物：
  描述：

  (4S,5S,E)-ethyl 7-(benzyloxy)-5-hydroxy-4-methylhept-2-enoate 在 甲醇 、 magnesium 作用下， 反应 5.0h， 以86%的产率得到(4S,5S)-ethyl 7-(benzyloxy)-5-hydroxy-4-methylheptanoate
  参考文献：
  名称：

  Novel iodine catalyzed diastereoselective synthesis of trans-2,6-disubstituted tetrahydro-2H-pyrans: synthesis of C1–C13 fragment of bistramide-A

  摘要：

  A new method for the stereoselective synthesis of trans 2.6-disubstituted tetrahydro-2H-pyrans has been developed involving iodine catalyzed allylation of tetrahydro-2H-pyranol with excellent trans selectivity. The method was also applied toward the construction of C1-C13 fragment of bistramide-A in 11 steps with 21.4% overall yield. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.08.085

文献信息

• Novel iodine catalyzed diastereoselective synthesis of trans-2,6-disubstituted tetrahydro-2H-pyrans: synthesis of C1–C13 fragment of bistramide-A
  作者：Jhillu Singh Yadav、Eppa Gyanchander、Anand Kumar Mishra、Peddapuram Adithya、Saibal Das

  DOI：10.1016/j.tetlet.2013.08.085

  日期：2013.10

  A new method for the stereoselective synthesis of trans 2.6-disubstituted tetrahydro-2H-pyrans has been developed involving iodine catalyzed allylation of tetrahydro-2H-pyranol with excellent trans selectivity. The method was also applied toward the construction of C1-C13 fragment of bistramide-A in 11 steps with 21.4% overall yield. (C) 2013 Elsevier Ltd. All rights reserved.