Carbamic acid (6Z,11Z)-(1S,2R,3R,4S,8S,9S,10S,13S)-3,13-bis-(tert-butyl-dimethyl-silanyloxy)-9-methoxymethoxy-2,4,6,8,10-pentamethyl-14-((2R,3S)-3-methyl-6-oxo-tetrahydro-pyran-2-yl)-1-((Z)-(S)-1-methyl-penta-2,4-dienyl)-tetradeca-6,11-dienyl ester | 870075-38-0

• 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: Carbamic acid (6Z,11Z)-(1S,2R,3R,4S,8S,9S,10S,13S)-3,13-bis-(tert-butyl-dimethyl-silanyloxy)-9-methoxymethoxy-2,4,6,8,10-pentamethyl-14-((2R,3S)-3-methyl-6-oxo-tetrahydro-pyran-2-yl)-1-((Z)-(S)-1-methyl-penta-2,4-dienyl)-tetradeca-6,11-dienyl ester
• CAS: 870075-38-0
• 化学式: C₄₆H₈₅NO₈Si₂
• 分子量: 836.354
• InChiKey: OEVOSDGONIKENV-DYWLYIIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.77
• 重原子数：
  57.0
• 可旋转键数：
  23.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  115.54
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  Carbamic acid (6Z,11Z)-(1S,2R,3R,4S,8S,9S,10S,13S)-3,13-bis-(tert-butyl-dimethyl-silanyloxy)-9-methoxymethoxy-2,4,6,8,10-pentamethyl-14-((2R,3S)-3-methyl-6-oxo-tetrahydro-pyran-2-yl)-1-((Z)-(S)-1-methyl-penta-2,4-dienyl)-tetradeca-6,11-dienyl ester 在 盐酸 作用下， 以65%的产率得到Carbamic acid (6Z,11Z)-(1S,2S,3R,4S,8S,9S,10S,13S)-3,9,13-trihydroxy-2,4,6,8,10-pentamethyl-14-((2R,3S)-3-methyl-6-oxo-tetrahydro-pyran-2-yl)-1-((Z)-(S)-1-methyl-penta-2,4-dienyl)-tetradeca-6,11-dienyl ester
  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：

  Acrylic acid (1R,2S)-1-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-propyl]-2-methyl-but-3-enyl ester 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 palladium dihydroxide 氢气 、 戴斯-马丁氧化剂 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 乙酸乙酯 为溶剂， 反应 2.0h， 生成 Carbamic acid (6Z,11Z)-(1S,2R,3R,4S,8S,9S,10S,13S)-3,13-bis-(tert-butyl-dimethyl-silanyloxy)-9-methoxymethoxy-2,4,6,8,10-pentamethyl-14-((2R,3S)-3-methyl-6-oxo-tetrahydro-pyran-2-yl)-1-((Z)-(S)-1-methyl-penta-2,4-dienyl)-tetradeca-6,11-dienyl ester
  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