(3R,4S,5S,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-3,5-dimethyl-6-[(3Z,8Z,16Z)-(2S,5S,6R,7S,11S,12R,13R,14S,15S)-2,6,12-tris-(tert-butyl-dimethyl-silanyloxy)-14-hydroxy-5,7,11,13,15-pentamethyl-nonadeca-3,8,16,18-tetraenyl]-tetrahydro-pyran-2-one | 835929-26-5

• 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,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-3,5-dimethyl-6-[(3Z,8Z,16Z)-(2S,5S,6R,7S,11S,12R,13R,14S,15S)-2,6,12-tris-(tert-butyl-dimethyl-silanyloxy)-14-hydroxy-5,7,11,13,15-pentamethyl-nonadeca-3,8,16,18-tetraenyl]-tetrahydro-pyran-2-one
• CAS: 835929-26-5
• 化学式: C₅₅H₁₀₈O₇Si₄
• 分子量: 993.8
• InChiKey: CHEIKPOZNVDAOQ-BKQKGDKSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.92
• 重原子数：
  66.0
• 可旋转键数：
  23.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  83.45
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (3R,4S,5S,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-3,5-dimethyl-6-[(3Z,8Z,16Z)-(2S,5S,6R,7S,11S,12R,13R,14S,15S)-2,6,12-tris-(tert-butyl-dimethyl-silanyloxy)-14-hydroxy-5,7,11,13,15-pentamethyl-nonadeca-3,8,16,18-tetraenyl]-tetrahydro-pyran-2-one 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以84%的产率得到(3R,4S,5R,6S)-4-hydroxy-3,5-dimethyl-6-[(2S,3Z,5S,6R,7S,8Z,11S,12R,13S,14S,15S,16Z)-2,6,12,14-tetrahydroxy-5,7,11,13,15-pentamethylnonadeca-3,8,16,18-tetraenyl]oxan-2-one
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of Carbamate-Substituted Analogues of (+)-Discodermolide

  摘要：

  The design, syntheses, and biological evaluation of 22 totally synthetic analogues of the potent microtubule-stabilizing agent (divided by)-discodermolide (1) have been achieved. Structure-activity relationships of the C(19) carbamate were defined. exploiting two synthetically simplified scaffolds. as well as the parent (+)-discodermolide framework.

  DOI：

  10.1021/ol047686a
• 作为产物：
  描述：

  (5Z,13Z)-(2S,3R,4S,8S,9R,10R,11S,12S)-3,9-Bis-(tert-butyl-dimethyl-silanyloxy)-11-(4-methoxy-benzyloxy)-2,4,8,10,12-pentamethyl-hexadeca-5,13,15-trien-1-ol 在 水 、 碘 、 sodium hexamethyldisilazane 、 N,N-二异丙基乙胺 、 三苯基膦 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 12.75h， 生成 (3R,4S,5S,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-3,5-dimethyl-6-[(3Z,8Z,16Z)-(2S,5S,6R,7S,11S,12R,13R,14S,15S)-2,6,12-tris-(tert-butyl-dimethyl-silanyloxy)-14-hydroxy-5,7,11,13,15-pentamethyl-nonadeca-3,8,16,18-tetraenyl]-tetrahydro-pyran-2-one
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of Carbamate-Substituted Analogues of (+)-Discodermolide

  摘要：

  The design, syntheses, and biological evaluation of 22 totally synthetic analogues of the potent microtubule-stabilizing agent (divided by)-discodermolide (1) have been achieved. Structure-activity relationships of the C(19) carbamate were defined. exploiting two synthetically simplified scaffolds. as well as the parent (+)-discodermolide framework.

  DOI：

  10.1021/ol047686a

文献信息

• Design, Synthesis, and Biological Evaluation of Potent Discodermolide Fluorescent and Photoaffinity Molecular Probes
  作者：Amos B. Smith、Paul V. Rucker、Ignacio Brouard、B. Scott Freeze、Shujun Xia、Susan Band Horwitz

  DOI：10.1021/ol0520166

  日期：2005.11.1

  [structure: see text] The design, synthesis, and biological evaluation of a series of (+)-discodermolide molecular probes possessing photoaffinity and fluorescent appendages has been achieved. Stereoselective olefin cross-metathesis comprised a key tactic for construction of two of the molecular probes. Three photoaffinity probes were radiolabeled with tritium.

  [结构：见正文]已经完成了一系列具有光亲和性和荧光附件的（+）-discodermolide分子探针的设计，合成和生物学评估。立体选择性烯烃交叉复分解是构建两个分子探针的关键策略。用tri对三种光亲和探针进行放射性标记。
• Design, Synthesis, and Evaluation of Analogues of (+)-14-Normethyldiscodermolide
  作者：Amos B. Smith、B. Scott Freeze、Matthew J. LaMarche、Tomoyasu Hirose、Ignacio Brouard、Ming Xian、Kurt F. Sundermann、Simon J. Shaw、Mark A. Burlingame、Susan Band Horwitz、David C. Myles

  DOI：10.1021/ol0476873

  日期：2005.1.1

  The design, syntheses, and biological evaluation of nine totally synthetic analogues of the microtubule-stabilizing agent (divided by)-14-normethyldiscodermolide (2) are reported. Simplification at the C(21)-C(24) terminal diene and at the C(1)-C(5) lactone moieties reveals significant structure-activity relationships.