(2S,8R,9R)-2-((tert-butyldimethylsilyl)oxy)-8-methyl-9-((tetrahydropyran-2-yl)oxy)decanal | 1206551-66-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,8R,9R)-2-((tert-butyldimethylsilyl)oxy)-8-methyl-9-((tetrahydropyran-2-yl)oxy)decanal
• CAS: 1206551-66-7
• 化学式: C₂₂H₄₄O₄Si
• 分子量: 400.674
• InChiKey: OWQNZNUVCWQPQB-MQEZQYLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.09
• 重原子数：
  27.0
• 可旋转键数：
  12.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2S,8R,9R)-2-((tert-butyldimethylsilyl)oxy)-8-methyl-9-((tetrahydropyran-2-yl)oxy)decanal 、 甲基三苯基溴化膦 在 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 为溶剂， 以86%的产率得到(3S,9R,10R)-3-((tert-butyldimethylsilyl)oxy)-9-methyl-10-((tetrahydropyran-2-yl)oxy)undec-1-ene
  参考文献：
  名称：

  Total synthesis of diastereomeric marine butenolides possessing a syn-aldol subunit at C10 and C11 and the related C11-ketone

  摘要：

  Two diastereomeric marine butenolides. (4S,10R,11R)- and (4S,10S,11S)-4,11-dihydroxy-10-methyldodec2-en-1,4-olide, possessing a syn-aldol subunit at C10 and C11 have been efficiently synthesized by using a three-module coupling strategy. The enantiomeric syn-aldol modules prepared by the syn-selective aldol reaction of the norephedrine-derived chiral propionates were coupled with the chiral C3-C7 module via 1,3-dithiane bisalkylation. The butenolide ring was then installed via a high-yielding ring-closing metathesis (RCM) reaction. Oxidation of the diastereomeric C11-alcohols furnished the corresponding C11-ketones, which are produced by the same marine microorganism. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.10.115
• 作为产物：
  描述：

  (2S,8R,9R)-2-((tert-butyldimethylsilyl)oxy)-8-methyl-9-((tetrahydropyran-2-yl)oxy)decan-1-ol 在 碳酸氢钠 、 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以87%的产率得到(2S,8R,9R)-2-((tert-butyldimethylsilyl)oxy)-8-methyl-9-((tetrahydropyran-2-yl)oxy)decanal
  参考文献：
  名称：

  Total synthesis of diastereomeric marine butenolides possessing a syn-aldol subunit at C10 and C11 and the related C11-ketone

  摘要：

  Two diastereomeric marine butenolides. (4S,10R,11R)- and (4S,10S,11S)-4,11-dihydroxy-10-methyldodec2-en-1,4-olide, possessing a syn-aldol subunit at C10 and C11 have been efficiently synthesized by using a three-module coupling strategy. The enantiomeric syn-aldol modules prepared by the syn-selective aldol reaction of the norephedrine-derived chiral propionates were coupled with the chiral C3-C7 module via 1,3-dithiane bisalkylation. The butenolide ring was then installed via a high-yielding ring-closing metathesis (RCM) reaction. Oxidation of the diastereomeric C11-alcohols furnished the corresponding C11-ketones, which are produced by the same marine microorganism. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.10.115