(2S,4R,5R)-2-[3-(t-butoxycarbonyl)-2-propenyl]-5-(t-butyldiphenylsilyloxy)-4-heptanolide | 877762-64-6

• 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: (2S,4R,5R)-2-[3-(t-butoxycarbonyl)-2-propenyl]-5-(t-butyldiphenylsilyloxy)-4-heptanolide
• 英文别名: tert-butyl (E)-4-[(3S,5R)-5-[(1R)-1-[tert-butyl(diphenyl)silyl]oxypropyl]-2-oxooxolan-3-yl]but-2-enoate
• CAS: 877762-64-6
• 化学式: C₃₁H₄₂O₅Si
• 分子量: 522.757
• InChiKey: BFMDENWCLAJQAK-YOAUKWABSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.56
• 重原子数：
  37
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,4R,5R)-2-[3-(t-butoxycarbonyl)-2-propenyl]-5-(t-butyldiphenylsilyloxy)-4-heptanolide 在 二异丁基氢化铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 0.33h， 生成 tert-butyl (E)-4-[(3S,5R)-5-[(1R)-1-[tert-butyl(diphenyl)silyl]oxypropyl]-2-hydroxyoxolan-3-yl]but-2-enoate
  参考文献：
  名称：

  Stereochemical revision of communiols D and H through synthesis

  摘要：

  Based on the previously revised stereochemistries for communiols A-C, the ent-8-epi- and ent-6-epi-stereoisomers of the original structures proposed for communiols D and H, respectively, were synthesized as highly probable candidates for their genuine structures by using the Sharpless asymmetric dihydroxylation as the source of chirality. Complete accord in spectral properties between each synthetic candidate and the corresponding natural material as well as the fact that communiols A-D and H were all isolated from the same fungal source, led us to the conclusion that the stereochemistries of communiols D and H should also be revised to their (3S,5S,7R,8S, 11R)and (5S,7R,8S)-forms, respectively. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.10.078
• 作为产物：
  描述：

  (4R,5R)-(-)-hydroxy-5 heptanolide-4 在 咪唑 、 臭氧 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 40.79h， 生成 (2S,4R,5R)-2-[3-(t-butoxycarbonyl)-2-propenyl]-5-(t-butyldiphenylsilyloxy)-4-heptanolide
  参考文献：
  名称：

  Stereochemical revision of communiols D and H through synthesis

  摘要：

  Based on the previously revised stereochemistries for communiols A-C, the ent-8-epi- and ent-6-epi-stereoisomers of the original structures proposed for communiols D and H, respectively, were synthesized as highly probable candidates for their genuine structures by using the Sharpless asymmetric dihydroxylation as the source of chirality. Complete accord in spectral properties between each synthetic candidate and the corresponding natural material as well as the fact that communiols A-D and H were all isolated from the same fungal source, led us to the conclusion that the stereochemistries of communiols D and H should also be revised to their (3S,5S,7R,8S, 11R)and (5S,7R,8S)-forms, respectively. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.10.078

文献信息

• Stereochemical revision of communiols D and H through synthesis
  作者：Masaru Enomoto、Takashi Nakahata、Shigefumi Kuwahara

  DOI：10.1016/j.tet.2005.10.078

  日期：2006.2

  Based on the previously revised stereochemistries for communiols A-C, the ent-8-epi- and ent-6-epi-stereoisomers of the original structures proposed for communiols D and H, respectively, were synthesized as highly probable candidates for their genuine structures by using the Sharpless asymmetric dihydroxylation as the source of chirality. Complete accord in spectral properties between each synthetic candidate and the corresponding natural material as well as the fact that communiols A-D and H were all isolated from the same fungal source, led us to the conclusion that the stereochemistries of communiols D and H should also be revised to their (3S,5S,7R,8S, 11R)and (5S,7R,8S)-forms, respectively. (c) 2005 Elsevier Ltd. All rights reserved.