(6R,7S,2E,8E)-7-(tert-butyldimethylsilyloxy)-5-oxo-2,6,8-trimethyl-2,8-decadienoic acid methyl ester | 760985-12-4

• 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: (6R,7S,2E,8E)-7-(tert-butyldimethylsilyloxy)-5-oxo-2,6,8-trimethyl-2,8-decadienoic acid methyl ester
• 英文别名: methyl (2E,6R,7S,8E)-7-[tert-butyl(dimethyl)silyl]oxy-2,6,8-trimethyl-5-oxodeca-2,8-dienoate
• CAS: 760985-12-4
• 化学式: C₂₀H₃₆O₄Si
• 分子量: 368.589
• InChiKey: UCUAQNXUCHPHIJ-KXMOCTPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.06
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (6R,7S,2E,8E)-7-(tert-butyldimethylsilyloxy)-5-oxo-2,6,8-trimethyl-2,8-decadienoic acid methyl ester 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以85%的产率得到(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
• 作为产物：
  描述：

  (2R,3S,4E)-3-(tert-butyldimethylsilyloxy)-2,4-dimethyl-4-hexenal 在 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 乙醚 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 2.5h， 生成 (6R,7S,2E,8E)-7-(tert-butyldimethylsilyloxy)-5-oxo-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

• 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.