1,11-dibenzyloxy 2R,10S-di-(t-butyldimethylsiloxy)-6-undecanol | 253184-98-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,11-dibenzyloxy 2R,10S-di-(t-butyldimethylsiloxy)-6-undecanol
• 英文别名: (2R,10R)-2,10-bis[[tert-butyl(dimethyl)silyl]oxy]-1,11-bis(phenylmethoxy)undecan-6-ol
• CAS: 253184-98-4
• 化学式: C₃₇H₆₄O₅Si₂
• 分子量: 645.083
• InChiKey: MTPGOKLOCSTABJ-VSJLXWSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.9
• 重原子数：
  44
• 可旋转键数：
  22
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,11-dibenzyloxy 2R,10S-di-(t-butyldimethylsiloxy)-6-undecanol 在 草酰氯 、 4,4'-di(tert-butyl)-[1,1-biphenyl]yllithium 、 氢氟酸 、 二甲基亚砜 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 0.5h， 生成 [(2R,8R)-8-(hydroxymethyl)-1,7-dioxaspiro[5,5]undec-2-yl]methan-1-ol
  参考文献：
  名称：

  Stereocontrolled synthesis of a novel pharmacophore of the tubulin-depolymerizing marine natural product spongistatin

  摘要：

  We report here the synthesis and X-ray structure of a novel spiroketal pyran, SPIKET-P1, as a pharmocophore for the tubulin-depolymerizing marine natural product spongistatin 1. Following its retro-synthetic analysis, SPIKET-P1 was prepared using a versatile 11-step synthetic scheme in a stereocontrolled fashion. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00054-x
• 作为产物：
  描述：

  (R)-苄氧甲基环氧乙烷 在 咪唑 、 4-二甲氨基吡啶 、 硼烷四氢呋喃络合物 、 magnesium 、 三乙胺 、 copper(I) bromide 、 lithium bromide 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 8.5h， 生成 1,11-dibenzyloxy 2R,10S-di-(t-butyldimethylsiloxy)-6-undecanol
  参考文献：
  名称：

  Stereocontrolled synthesis of a novel pharmacophore of the tubulin-depolymerizing marine natural product spongistatin

  摘要：

  We report here the synthesis and X-ray structure of a novel spiroketal pyran, SPIKET-P1, as a pharmocophore for the tubulin-depolymerizing marine natural product spongistatin 1. Following its retro-synthetic analysis, SPIKET-P1 was prepared using a versatile 11-step synthetic scheme in a stereocontrolled fashion. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00054-x

文献信息

• Synthetic spiroketal pyranes as potent anti-cancer agents
  申请人：Parker Hughes Institute

  公开号：US06335364B1

  公开（公告）日：2002-01-01

  Novel tubulin binding compounds (SPIKETS) having potent tubulin depolymerization activity and inhibitory activity against tubulin polymerization. The compounds are effective agents for inhibiting cellular proliferation, for example, in cancer cells. The compounds are adapted to interact favorably with a novel SP binding pocket on tubulin, which pocket is useful for screening of anti-tubulin, anti-proliferation, and anti-cancer drugs.

  具有强大的微管去聚合活性和抑制微管聚合活性的新型微管结合化合物（SPIKETS）。这些化合物是有效的抑制细胞增殖的药剂，例如在癌细胞中。这些化合物适应与微管上的新型SP结合口袋有利地相互作用，该口袋可用于筛选抗微管、抗增殖和抗癌药物。
• Stereocontrolled synthesis of a novel pharmacophore of the tubulin-depolymerizing marine natural product spongistatin
  作者：He Huang、Chen Mao、Shyi-Tai Jan、Fatih M Uckun

  DOI：10.1016/s0040-4039(00)00054-x

  日期：2000.3

  We report here the synthesis and X-ray structure of a novel spiroketal pyran, SPIKET-P1, as a pharmocophore for the tubulin-depolymerizing marine natural product spongistatin 1. Following its retro-synthetic analysis, SPIKET-P1 was prepared using a versatile 11-step synthetic scheme in a stereocontrolled fashion. (C) 2000 Elsevier Science Ltd. All rights reserved.