(S)-2-(tert-Butyl-dimethyl-silanyloxy)-3-((2S,3R)-3-methyl-6-oxo-tetrahydro-pyran-2-yl)-propionaldehyde | 853055-22-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (S)-2-(tert-Butyl-dimethyl-silanyloxy)-3-((2S,3R)-3-methyl-6-oxo-tetrahydro-pyran-2-yl)-propionaldehyde
• CAS: 853055-22-8
• 化学式: C₁₅H₂₈O₄Si
• 分子量: 300.47
• InChiKey: QVZXFEJSGHKIRK-AGIUHOORSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.31
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (S)-2-(tert-Butyl-dimethyl-silanyloxy)-3-((2S,3R)-3-methyl-6-oxo-tetrahydro-pyran-2-yl)-propionaldehyde 在 甲基锂 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 生成 (5R,6S)-6-[(3Z,8Z,16Z)-(2S,5S,6S,7S,11S,12R,13R,14S,15S)-2,12-Bis-(tert-butyl-dimethyl-silanyloxy)-14-hydroxy-6-methoxymethoxy-5,7,9,11,13,15-hexamethyl-nonadeca-3,8,16-trienyl]-5-methyl-tetrahydro-pyran-2-one
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of Simplified Analogues of (+)-Discodermolide. Additional Insights on the Importance of the Diene, the C(7) Hydroxyl, and the Lactone

  摘要：

  The design, synthesis, and biological evaluation of seven totally synthetic analogues of the antitumor agent (+)-discodermolide are reported. lid Saturation of the terminal diene system, alteration of the substituents on the lactone, and alkylation of the C(7)-hydroxyl group reveal significant structure-activity relationships.

  DOI：

  10.1021/ol052070m
• 作为产物：
  描述：

  (5R,6S)-6-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-propyl]-5-methyl-5,6-dihydro-pyran-2-one 在 palladium dihydroxide 氢气 、 碳酸氢钠 、 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 4.5h， 生成 (S)-2-(tert-Butyl-dimethyl-silanyloxy)-3-((2S,3R)-3-methyl-6-oxo-tetrahydro-pyran-2-yl)-propionaldehyde
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of Simplified Analogues of (+)-Discodermolide. Additional Insights on the Importance of the Diene, the C(7) Hydroxyl, and the Lactone

  摘要：

  The design, synthesis, and biological evaluation of seven totally synthetic analogues of the antitumor agent (+)-discodermolide are reported. lid Saturation of the terminal diene system, alteration of the substituents on the lactone, and alkylation of the C(7)-hydroxyl group reveal significant structure-activity relationships.

  DOI：

  10.1021/ol052070m

文献信息

• Toward Understanding How the Lactone Moiety of Discodermolide Affects Activity
  作者：Simon J. Shaw、Kurt F. Sundermann、Mark A. Burlingame、David C. Myles、B. Scott Freeze、Ming Xian、Ignacio Brouard、Amos B. Smith

  DOI：10.1021/ja051185i

  日期：2005.5.1

  A series of simplified discodermolide analogues have been designed and synthesized in an attempt to understand the role of the lactone ring. These synthetic efforts have led to an unsubstituted butyrolactone 9 being generated, which shows improved activity over the natural product.