(5S,6S,7S,2E,8E)-7-(tert-butyldimethylsilyloxy)-5-hydroxy-2,6,8-trimethyl-2,8-decadienoic acid methyl ester | 760984-40-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (5S,6S,7S,2E,8E)-7-(tert-butyldimethylsilyloxy)-5-hydroxy-2,6,8-trimethyl-2,8-decadienoic acid methyl ester
• 英文别名: methyl (2E,5S,6S,7S,8E)-7-[tert-butyl(dimethyl)silyl]oxy-5-hydroxy-2,6,8-trimethyldeca-2,8-dienoate
• CAS: 760984-40-5
• 化学式: C₂₀H₃₈O₄Si
• 分子量: 370.605
• InChiKey: XBNUYTYVDUHMLO-ANQKNTQUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.85
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (5S,6S,7S,2E,8E)-7-(tert-butyldimethylsilyloxy)-5-hydroxy-2,6,8-trimethyl-2,8-decadienoic acid methyl ester 在 4-甲基苯磺酸吡啶 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 2.0h， 生成 (5S,6S,7S,2E,8E)-2,6,8-trimethyl-2,8-decadien-1,5,7-triol
  参考文献：
  名称：

  Kulokekahilide-2, a Cytotoxic Depsipeptide from a Cephalaspidean Mollusk Philinopsis speciosa

  摘要：

  A cytotoxic depsipeptide, kulokekahilide-2 (1), was isolated from a cephalaspidean mollusk, Philinopsis speciosa. The structure elucidation of kulokekahilide-2 was carried out by spectroscopic analysis and chemical degradation. Kulokekahilide-2 showed potent cytotoxicity against several cell lines (P388, SKOV-3, MDA-MB-435, and A-10 with IC50 values ranging from 4.2 to 59.1 nM) indicating cancer cell selectivity.

  DOI：

  10.1021/np049949f
• 作为产物：
  描述：

  (2R,3S,4E)-3-(tert-butyldimethylsilyloxy)-2,4-dimethyl-4-hexenal 在 sodium tetrahydroborate 、 三氟化硼乙醚 、 三氟乙酸吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 4.5h， 生成 (5S,6S,7S,2E,8E)-7-(tert-butyldimethylsilyloxy)-5-hydroxy-2,6,8-trimethyl-2,8-decadienoic acid methyl ester
  参考文献：
  名称：

  Kulokekahilide-2, a Cytotoxic Depsipeptide from a Cephalaspidean Mollusk Philinopsis speciosa

  摘要：

  A cytotoxic depsipeptide, kulokekahilide-2 (1), was isolated from a cephalaspidean mollusk, Philinopsis speciosa. The structure elucidation of kulokekahilide-2 was carried out by spectroscopic analysis and chemical degradation. Kulokekahilide-2 showed potent cytotoxicity against several cell lines (P388, SKOV-3, MDA-MB-435, and A-10 with IC50 values ranging from 4.2 to 59.1 nM) indicating cancer cell selectivity.

  DOI：

  10.1021/np049949f

文献信息

• Reinvestigation of the stereochemistry of kulokekahilide-2
  作者：Yuuki Takada、Eriko Mori、Masahiro Umehara、Yoichi Nakao、Junji Kimura

  DOI：10.1016/j.tetlet.2007.08.093

  日期：2007.10

  An attempt to carry out a total synthesis of kulokekahilide-2 (1) by macrolactonization of a seco acid prepared from a suitably protected hexapeptide and a dioxy acid moiety unexpectedly resulted in the formation of the 43-epimer (1a) of the cytotoxic depsipeptide, for which structure 1b has previously been proposed. A second attempt involving macrolactamization of the corresponding amino acid gave the target product, 1b, but the spectral data of the product did not match those of natural 1. Furthermore, neither la nor 1b showed any cytotoxicity, from which it is concluded that the structure of natural I is incorrect and should be re-examined. (C) 2007 Elsevier Ltd. All rights reserved.
• Kulokekahilide-2, a Cytotoxic Depsipeptide from a Cephalaspidean Mollusk <i>Philinopsis speciosa</i>
  作者：Yoichi Nakao、Wesley Y. Yoshida、Yuuki Takada、Junji Kimura、Liu Yang、Susan L. Mooberry、Paul J. Scheuer

  DOI：10.1021/np049949f

  日期：2004.8.1

  A cytotoxic depsipeptide, kulokekahilide-2 (1), was isolated from a cephalaspidean mollusk, Philinopsis speciosa. The structure elucidation of kulokekahilide-2 was carried out by spectroscopic analysis and chemical degradation. Kulokekahilide-2 showed potent cytotoxicity against several cell lines (P388, SKOV-3, MDA-MB-435, and A-10 with IC50 values ranging from 4.2 to 59.1 nM) indicating cancer cell selectivity.