(E)-(4R,5R,11S)-methyl 11-acetoxy-5-(tert-butyldiphenylsilyloxy)-4-((2-methoxyethoxy)methoxy)-2-dodecenoate | 1107608-31-0

• 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: (E)-(4R,5R,11S)-methyl 11-acetoxy-5-(tert-butyldiphenylsilyloxy)-4-((2-methoxyethoxy)methoxy)-2-dodecenoate
• 英文别名: methyl (E,4R,5R,11S)-11-acetyloxy-5-[tert-butyl(diphenyl)silyl]oxy-4-(2-methoxyethoxymethoxy)dodec-2-enoate
• CAS: 1107608-31-0
• 化学式: C₃₅H₅₂O₈Si
• 分子量: 628.879
• InChiKey: HDORUFHUSNBIOC-RISYEXPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.57
• 重原子数：
  44
• 可旋转键数：
  23
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  89.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (E)-(4R,5R,11S)-methyl 11-acetoxy-5-(tert-butyldiphenylsilyloxy)-4-((2-methoxyethoxy)methoxy)-2-dodecenoate 在 lithium hydroxide 、 水 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 16.0h， 以99%的产率得到(E)-(4R,5R,11S)-5-(tert-butyldiphenylsilyloxy)-11-hydroxy-4-((2-methoxyethoxy)methoxy)-2-dodecenoic acid
  参考文献：
  名称：

  Synthesis and stereochemical assignment of (+)-Cladospolide D

  摘要：

  Cladospolides A-D are 12-membered, alpha,beta-unsaturated lactones isolated from various species of Cladosporium. Cladospolide D is unique in its gamma-keto functionality and possesses antifungal activity; however, the stereochemistry of Cladoapolide D was unknown. We report the asymmetric syntheses to generate both possible diastereomers of Cladospolide D. Two regioselective cross-metatheses were applied to form the carbon skeleton, and the two olefins were differentiated by Michael addition, hydrogenation, and elimination. Later, the macrocycle was achieved through the Yamaguchi protocol. After comparing the spectroscopic data of the synthetic Cladospolide D with the reported values, the stereochemistry of Cladospolide D is confirmed as (2E,5R,11S). (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.10.059
• 作为产物：
  描述：

  methyl (4S,5R,11S)-11-acetyloxy-5-[tert-butyl(diphenyl)silyl]oxy-3-butylsulfonyl-4-(2-methoxyethoxymethoxy)dodecanoate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯氟甲烷 为溶剂， 反应 1.0h， 以50.5 mg的产率得到(E)-(4R,5R,11S)-methyl 11-acetoxy-5-(tert-butyldiphenylsilyloxy)-4-((2-methoxyethoxy)methoxy)-2-dodecenoate
  参考文献：
  名称：

  Synthesis and stereochemical assignment of (+)-Cladospolide D

  摘要：

  Cladospolides A-D are 12-membered, alpha,beta-unsaturated lactones isolated from various species of Cladosporium. Cladospolide D is unique in its gamma-keto functionality and possesses antifungal activity; however, the stereochemistry of Cladoapolide D was unknown. We report the asymmetric syntheses to generate both possible diastereomers of Cladospolide D. Two regioselective cross-metatheses were applied to form the carbon skeleton, and the two olefins were differentiated by Michael addition, hydrogenation, and elimination. Later, the macrocycle was achieved through the Yamaguchi protocol. After comparing the spectroscopic data of the synthetic Cladospolide D with the reported values, the stereochemistry of Cladospolide D is confirmed as (2E,5R,11S). (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.10.059