(3R,4S,5S,6R)-4-[(E)-1,5-dimethylhex-1-enyl]-5-methoxy-6-p-methoxybenzyloxy-1-oxaspiro[2.5]octane | 527754-99-0

• 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: (3R,4S,5S,6R)-4-[(E)-1,5-dimethylhex-1-enyl]-5-methoxy-6-p-methoxybenzyloxy-1-oxaspiro[2.5]octane
• 英文别名: (3R,4S,5S,6R)-5-methoxy-6-[(4-methoxyphenyl)methoxy]-4-[(E)-6-methylhept-2-en-2-yl]-1-oxaspiro[2.5]octane
• CAS: 527754-99-0
• 化学式: C₂₄H₃₆O₄
• 分子量: 388.547
• InChiKey: RXGYHOYOWVCOAE-RAYGXKAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  40.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3R,4S,5S,6R)-4-[(E)-1,5-dimethylhex-1-enyl]-5-methoxy-6-p-methoxybenzyloxy-1-oxaspiro[2.5]octane 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 1.5h， 生成 (3R,4S,5S,6R)-4-((E)-1,5-Dimethyl-hex-1-enyl)-5-methoxy-1-oxa-spiro[2.5]octan-6-ol
  参考文献：
  名称：

  MetAP-2 Inhibitors Based on the Fumagillin Structure. Side-Chain Modification and Ring-Substituted Analogues

  摘要：

  The preparation of a series of new fumagillin-derived MetAP-2 inhibitors is described. The synthetic approach was designed so as to permit modification of the fumagillin backbone at sites inaccessible through semisynthesis or previously existing total syntheses. An Evans aldolization and a ring-closing metathesis allowed the preparation of a pivotal intermediate which could then be functionalized in various ways using already established or newly developed methodologies.

  DOI：

  10.1021/jo035065+
• 作为产物：
  描述：

  (E)-4-iodo-3-methylbut-3-en-1-ol 在 镍 咪唑 、 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 chromium(VI) oxide 、 正丁基锂 、 草酰氯 、 硫酸 、 四丁基氟化铵 、 三甲基铝 、 sodium hydride 、 四丁基高碘酸铵 、 magnesium 、 N,N-二甲基甲酰胺 、 silver(l) oxide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 、 氯仿 、 水 、 二甲基亚砜 、 丙酮 、 甲苯 为溶剂， 反应 76.5h， 生成 (3R,4S,5S,6R)-4-[(E)-1,5-dimethylhex-1-enyl]-5-methoxy-6-p-methoxybenzyloxy-1-oxaspiro[2.5]octane
  参考文献：
  名称：

  MetAP-2 Inhibitors Based on the Fumagillin Structure. Side-Chain Modification and Ring-Substituted Analogues

  摘要：

  The preparation of a series of new fumagillin-derived MetAP-2 inhibitors is described. The synthetic approach was designed so as to permit modification of the fumagillin backbone at sites inaccessible through semisynthesis or previously existing total syntheses. An Evans aldolization and a ring-closing metathesis allowed the preparation of a pivotal intermediate which could then be functionalized in various ways using already established or newly developed methodologies.

  DOI：

  10.1021/jo035065+

文献信息

• Novel angiogenesis inhibitors and pharmaceutical and cosmetic use thereof
  申请人：——

  公开号：US20030134896A1

  公开（公告）日：2003-07-17

  The invention relates to novel 1-oxaspiro[2,5]octan-6-ol derivatives of general formula (1): 1 and also to a method for preparing them, and to their use in pharmaceutical compositions for use in human or veterinary medicine, or in cosmetic compositions.

  这项发明涉及一种新型的一氧杂螺[2,5]辛烷-6-醇衍生物，其一般化学式为(1):1，以及制备这些衍生物的方法，以及它们在用于人类或兽医药物中的药用组合物或化妆品组合物中的用途。
• US6803382B2
  申请人：——

  公开号：US6803382B2

  公开（公告）日：2004-10-12
• MetAP-2 Inhibitors Based on the Fumagillin Structure. Side-Chain Modification and Ring-Substituted Analogues
  作者：Vincent Rodeschini、Jean-Guy Boiteau、Pierre Van de Weghe、Céline Tarnus、Jacques Eustache

  DOI：10.1021/jo035065+

  日期：2004.1.1

  The preparation of a series of new fumagillin-derived MetAP-2 inhibitors is described. The synthetic approach was designed so as to permit modification of the fumagillin backbone at sites inaccessible through semisynthesis or previously existing total syntheses. An Evans aldolization and a ring-closing metathesis allowed the preparation of a pivotal intermediate which could then be functionalized in various ways using already established or newly developed methodologies.