(E)-(5R,6R,12S)-6-(tert-butyldiphenylsilyloxy)-5-((2-methoxyethoxy)methoxy)-12-methyloxacyclododec-3-en-2-one | 1107608-33-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: (E)-(5R,6R,12S)-6-(tert-butyldiphenylsilyloxy)-5-((2-methoxyethoxy)methoxy)-12-methyloxacyclododec-3-en-2-one
• 英文别名: (3E,5R,6R,12S)-6-[tert-butyl(diphenyl)silyl]oxy-5-(2-methoxyethoxymethoxy)-12-methyl-1-oxacyclododec-3-en-2-one
• CAS: 1107608-33-2
• 化学式: C₃₂H₄₆O₆Si
• 分子量: 554.799
• InChiKey: YGWJCDAGMXPTMR-HZQKXDHYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.39
• 重原子数：
  39
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (E)-(5R,6R,12S)-6-(tert-butyldiphenylsilyloxy)-5-((2-methoxyethoxy)methoxy)-12-methyloxacyclododec-3-en-2-one 在 B-溴代邻苯二氧硼烷 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以98%的产率得到(E)-(5R,6R,12S)-6-(tert-butyldiphenylsilyloxy)-5-hydroxy-12-methyloxacyclododec-3-en-2-one
  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：

  (E)-(4R,5R,11S)-5-(tert-butyldiphenylsilyloxy)-11-hydroxy-4-((2-methoxyethoxy)methoxy)-2-dodecenoic acid 在 2,4,6-三氯苯甲酰氯 、 三乙胺 、 4-二甲氨基吡啶 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 6.0h， 以78%的产率得到(E)-(5R,6R,12S)-6-(tert-butyldiphenylsilyloxy)-5-((2-methoxyethoxy)methoxy)-12-methyloxacyclododec-3-en-2-one
  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

文献信息

• Synthesis and stereochemical assignment of (+)-Cladospolide D
  作者：Ke-Jhen Lu、Chia-Hsiu Chen、Duen-Ren Hou

  DOI：10.1016/j.tet.2008.10.059

  日期：2009.1

  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.