(3R,4S,5S,6S,7S)-4-[(E)-1,5-dimethylhex-1-enyl]-7-(isopropyldimethylsilanyloxy)-5-methoxy-1-oxaspiro[2.5]octan-6-ol | 655253-36-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3R,4S,5S,6S,7S)-4-[(E)-1,5-dimethylhex-1-enyl]-7-(isopropyldimethylsilanyloxy)-5-methoxy-1-oxaspiro[2.5]octan-6-ol
• 英文别名: (3R,4S,5S,6S,7S)-7-[dimethyl(propan-2-yl)silyl]oxy-5-methoxy-4-[(E)-6-methylhept-2-en-2-yl]-1-oxaspiro[2.5]octan-6-ol
• CAS: 655253-36-4
• 化学式: C₂₁H₄₀O₄Si
• 分子量: 384.632
• InChiKey: FJZNYHRLLMVKRS-PNEDUOJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.53
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3R,4S,5S,6S,7S)-4-[(E)-1,5-dimethylhex-1-enyl]-7-(isopropyldimethylsilanyloxy)-5-methoxy-1-oxaspiro[2.5]octan-6-ol 在 4-二甲氨基吡啶 、 四丁基氟化铵 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 36.5h， 生成 (3R,4S,5S,6R,7S)-4-(1,5-dimethylhex-1-enyl)-7-hydroxy-5-methoxy-1-oxaspiro[2,5]oct-6-yl 4-methoxycinnamate
  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：

  (4R,5S,6S)-5-methoxy-4-p-methoxybenzyloxy-6-[(E)-1,5-dimethylhex-1-enyl]cyclohex-2-enone 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 正丁基锂 、 二苯基二硒醚 、 双氧水 、 potassium carbonate 、 溶剂黄146 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 正己烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.75h， 生成 (3R,4S,5S,6S,7S)-4-[(E)-1,5-dimethylhex-1-enyl]-7-(isopropyldimethylsilanyloxy)-5-methoxy-1-oxaspiro[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+