(3-imidazol-1-yl-propyl)-carbamic acid 3,9,13-tris-(tert-butyl-dimethyl-silanyloxy)-14-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-6-oxo-tetrahydro-pyran-2-yl]-2,4,6,8,10-pentamethyl-1-(1-methyl-penta-2,4-dienyl)-tetradeca-6,11-dienyl ester | 835929-74-3

• 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: (3-imidazol-1-yl-propyl)-carbamic acid 3,9,13-tris-(tert-butyl-dimethyl-silanyloxy)-14-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-6-oxo-tetrahydro-pyran-2-yl]-2,4,6,8,10-pentamethyl-1-(1-methyl-penta-2,4-dienyl)-tetradeca-6,11-dienyl ester
• CAS: 835929-74-3
• 化学式: C₆₃H₁₁₉N₃O₈Si₄
• 分子量: 1159.0
• InChiKey: HIKIFYOJPZMTCQ-ANKHNRLESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17.33
• 重原子数：
  78.0
• 可旋转键数：
  28.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  119.37
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (3-imidazol-1-yl-propyl)-carbamic acid 3,9,13-tris-(tert-butyl-dimethyl-silanyloxy)-14-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-6-oxo-tetrahydro-pyran-2-yl]-2,4,6,8,10-pentamethyl-1-(1-methyl-penta-2,4-dienyl)-tetradeca-6,11-dienyl ester 在 盐酸 作用下， 以 甲醇 为溶剂， 以62%的产率得到[(3Z,5S,6S,7S,8R,9S,11Z,13S,14S,15S,16Z,18S)-8,14,18-trihydroxy-19-[(2S,3R,4S,5R)-4-hydroxy-3,5-dimethyl-6-oxooxan-2-yl]-5,7,9,11,13,15-hexamethylnonadeca-1,3,11,16-tetraen-6-yl] N-(3-imidazol-1-ylpropyl)carbamate
  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：

  (3R,4S,5S,6S)-4-[tert-butyl(dimethyl)silyl]oxy-3,5-dimethyl-6-[(2S,3Z,5S,6S,7S,8Z,11S,12R,13R,14S,15S,16Z)-2,6,12-tris[[tert-butyl(dimethyl)silyl]oxy]-14-hydroxy-5,7,9,11,13,15-hexamethylnonadeca-3,8,16,18-tetraenyl]oxan-2-one 在 碘甲烷 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 18.0h， 生成 (3-imidazol-1-yl-propyl)-carbamic acid 3,9,13-tris-(tert-butyl-dimethyl-silanyloxy)-14-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-6-oxo-tetrahydro-pyran-2-yl]-2,4,6,8,10-pentamethyl-1-(1-methyl-penta-2,4-dienyl)-tetradeca-6,11-dienyl ester
  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