2-(2R,3S,6R)-3-hydroxy-6-[(E,6S)-6-hydroxy-1-heptenyl]tetrahydro-2H-2-pyranyl acetic acid | 1210969-65-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 2-(2R,3S,6R)-3-hydroxy-6-[(E,6S)-6-hydroxy-1-heptenyl]tetrahydro-2H-2-pyranyl acetic acid
• 英文别名: {(2R,3S,6R)-3-tert-butyldimethylsilyloxy-6-[(S)-6-hydroxy-1-heptenyl]tetrahydropyran-2-yl}acetic acid；2-[(2R,3S,6R)-3-[tert-butyl(dimethyl)silyl]oxy-6-[(E,6S)-6-hydroxyhept-1-enyl]oxan-2-yl]acetic acid
• CAS: 1210969-65-5
• 化学式: C₂₀H₃₈O₅Si
• 分子量: 386.604
• InChiKey: SSGCVTANVWAIGM-IUFWLWRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.51
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 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：

  2-(2R,3S,6R)-3-hydroxy-6-[(E,6S)-6-hydroxy-1-heptenyl]tetrahydro-2H-2-pyranyl acetic acid 在 4-二甲氨基吡啶 、 2-甲基-6-硝基苯甲酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 28.0h， 以22%的产率得到
  参考文献：
  名称：

  由曲霉内酯B的合成中间体合成曲霉内酯A

  摘要：

  曲霉内酯A的第一次合成是由海洋真菌产生的细胞毒素，它是由曲霉内酯B的合成中间体通过脯氨酸介导的2，6-反式取代的四氢吡喃-2-乙醛中间体差向异构化成相应的顺式异构体通过反-氧-迈克尔/氧-迈克尔序列作为关键转化。

  DOI：

  10.1016/j.tetlet.2009.12.032
• 作为产物：
  描述：

  在 甲醇 、 sodium chlorite 、 sodium dihydrogenphosphate 、 lithium aluminium tetrahydride 、 2-甲基-2-丁烯 、 三乙基硼 、 camphor-10-sulfonic acid 、 氧气 、 三正丁基氢锡 、 碳酸氢钠 、 戴斯-马丁氧化剂 、 三乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 D-脯氨酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 甲苯 、 叔丁醇 为溶剂， 反应 26.0h， 生成 2-(2R,3S,6R)-3-hydroxy-6-[(E,6S)-6-hydroxy-1-heptenyl]tetrahydro-2H-2-pyranyl acetic acid
  参考文献：
  名称：

  Synthesis of aspergillide A via proline-catalyzed trans-to-cis isomerization of a substituted tetrahydropyran

  摘要：

  The transformation of a common synthetic intermediate of aspergillides B and C into aspergillide A, a cytotoxin produced by a marine-derived fungus, has been accomplished in an eleven-step sequence involving an efficient proline-catalyzed isomerization of a 2,6-trans-substituted tetrahydropyran-2-acetaldehyde intermediate into the corresponding cis isomer and the Yamaguchi macrolactonization as the key steps. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.02.061

文献信息

• Synthesis of aspergillide A from a synthetic intermediate of aspergillide B
  作者：Tomohiro Nagasawa、Shigefumi Kuwahara

  DOI：10.1016/j.tetlet.2009.12.032

  日期：2010.2

  The first synthesis of aspergillide A, a cytotoxin produced by a marine-derived fungus, has been achieved from a synthetic intermediate of aspergillide B by using a proline-mediated epimerization of a 2,6-trans-substituted tetrahydropyran-2-acetaldehyde intermediate into the corresponding cis-isomer via a retro-oxy-Michael/oxy-Michael sequence as the key transformation.

  曲霉内酯A的第一次合成是由海洋真菌产生的细胞毒素，它是由曲霉内酯B的合成中间体通过脯氨酸介导的2，6-反式取代的四氢吡喃-2-乙醛中间体差向异构化成相应的顺式异构体通过反-氧-迈克尔/氧-迈克尔序列作为关键转化。
• Stereoselective formal synthesis of aspergillide A
  作者：Gowravaram Sabitha、D. Vasudeva Reddy、A. Senkara Rao、J.S. Yadav

  DOI：10.1016/j.tetlet.2010.06.013

  日期：2010.8

  The stereoselective formal synthesis of aspergillide A (1), a cytotoxic 14-membered macrolide, is disclosed. The key intermediate, a trisubstituted tetrahydropyran core is prepared by SmI(2)-induced intramolecular reductive cyclization as well as by using sequential alpha-aminooxylation, Homer-Wadsworth-Emmons olefination, and followed by Oxa-Michael cyclization. Other notable transformations in the synthesis include the use of Jacobsen's hydrolytic kinetic resolution, esterification, ring-closing metathesis (RCM), and cross-metathesis (CM) reactions. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis of aspergillide A via proline-catalyzed trans-to-cis isomerization of a substituted tetrahydropyran
  作者：Tomohiro Nagasawa、Tomoo Nukada、Shigefumi Kuwahara

  DOI：10.1016/j.tet.2011.02.061

  日期：2011.4

  The transformation of a common synthetic intermediate of aspergillides B and C into aspergillide A, a cytotoxin produced by a marine-derived fungus, has been accomplished in an eleven-step sequence involving an efficient proline-catalyzed isomerization of a 2,6-trans-substituted tetrahydropyran-2-acetaldehyde intermediate into the corresponding cis isomer and the Yamaguchi macrolactonization as the key steps. (C) 2011 Elsevier Ltd. All rights reserved.