3-O-(tert-butyldimethylsilyl)discodermolide

• 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: 3-O-(tert-butyldimethylsilyl)discodermolide
• 英文别名: [(3Z,5S,6S,7S,8R,9S,11Z,13S,14S,15S,16Z,18S)-19-[(2S,3S,4S,5R)-4-[tert-butyl(dimethyl)silyl]oxy-3,5-dimethyl-6-oxooxan-2-yl]-8,14,18-trihydroxy-5,7,9,11,13,15-hexamethylnonadeca-1,3,11,16-tetraen-6-yl] carbamate
• 化学式: C₃₉H₆₉NO₈Si
• 分子量: 708.064
• InChiKey: MUSLLNFAFAEMNK-JOMXDTENSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.33
• 重原子数：
  49
• 可旋转键数：
  20
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  149
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  carbamic acid (6Z,11Z)-(1S,2R,3R,4S,8S,9S,10S,-13S,15S,16S,17S,18R)-3,9,17-tris-(tert-butyldimethylsilanyloxy)-13,15-dihydroxy-18-(methoxymethylcarbamoyl)-2,4,6,8,10,16-hexamethyl-1-((Z)-(S)-1-methylpenta-2,4-dienyl)-nonadeca-6,11-dienyl ester 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 3-O-(tert-butyldimethylsilyl)discodermolide 、 盘皮海绵内酯 、 3,11,17-O-tris-(tert-butyldimethylsilyl)discodermolide
  参考文献：
  名称：

  Synthetic Analogues of the Microtubule-Stabilizing Agent (+)-Discodermolide:  Preparation and Biological Activity

  摘要：

  A series of seven synthetic discodermolide analogues 2-8, which are minor side products generated during the final stages in the synthesis of (+)-discodermolide (1), have been purified and evaluated for in vitro cytotoxicity against A549, P388, MFC-7, NCI/ADR, PANC-1, and VERO cell lines. These synthetic analogues showed a significant variation of cytotoxicity and confirmed the importance of the C-7 hydroxy through C-17 hydroxy molecular fragment for potency. Specifically, these analogues suggested the relevance of the C-11 hydroxyl group, the C-13 double bond, and the C-16 (S) stereochemistry for the potency of (+)-discodermolide. The preparation, purification, structure elucidation, and biological activity of these new analogues are described.

  DOI：

  10.1021/np030493w

文献信息

• Synthetic Analogues of the Microtubule-Stabilizing Agent (+)-Discodermolide:  Preparation and Biological Activity
  作者：Sarath P. Gunasekera、Stuart J. Mickel、Robert Daeffler、Daniel Niederer、Amy E. Wright、Patricia Linley、Tara Pitts

  DOI：10.1021/np030493w

  日期：2004.5.1

  A series of seven synthetic discodermolide analogues 2-8, which are minor side products generated during the final stages in the synthesis of (+)-discodermolide (1), have been purified and evaluated for in vitro cytotoxicity against A549, P388, MFC-7, NCI/ADR, PANC-1, and VERO cell lines. These synthetic analogues showed a significant variation of cytotoxicity and confirmed the importance of the C-7 hydroxy through C-17 hydroxy molecular fragment for potency. Specifically, these analogues suggested the relevance of the C-11 hydroxyl group, the C-13 double bond, and the C-16 (S) stereochemistry for the potency of (+)-discodermolide. The preparation, purification, structure elucidation, and biological activity of these new analogues are described.