2-[(2R,3R,6R)-3-[tert-butyl(dimethyl)silyl]oxy-6-[(E,6S)-6-hydroxyhept-1-enyl]oxan-2-yl]acetic acid | 1300040-13-4

• 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,3R,6R)-3-[tert-butyl(dimethyl)silyl]oxy-6-[(E,6S)-6-hydroxyhept-1-enyl]oxan-2-yl]acetic acid
• CAS: 1300040-13-4
• 化学式: C₂₀H₃₈O₅Si
• 分子量: 386.604
• InChiKey: SSGCVTANVWAIGM-BQHSMOHQSA-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,3R,6R)-3-[tert-butyl(dimethyl)silyl]oxy-6-[(E,6S)-6-hydroxyhept-1-enyl]oxan-2-yl]acetic acid 在 4-二甲氨基吡啶 、 2,4,6-三氯苯甲酰氯 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 13.0h， 生成 (1S,5S,11R,14R)-14-hydroxy-5-methyl-4,15-dioxabicyclo[9.3.1]pentadec-9-en-3-one
  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
• 作为产物：
  描述：

  在 水 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-[(2R,3R,6R)-3-[tert-butyl(dimethyl)silyl]oxy-6-[(E,6S)-6-hydroxyhept-1-enyl]oxan-2-yl]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 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.