(5R,6S)-3,5-Dimethyl-6-[(3Z,8Z,16Z)-(2S,5S,6S,7S,11S,12R,13R,14S,15S)-2,6,12-tris-(tert-butyl-dimethyl-silanyloxy)-14-hydroxy-5,7,9,11,13,15-hexamethyl-nonadeca-3,8,16,18-tetraenyl]-5,6-dihydro-pyran-2-one | 835929-40-3

• 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: (5R,6S)-3,5-Dimethyl-6-[(3Z,8Z,16Z)-(2S,5S,6S,7S,11S,12R,13R,14S,15S)-2,6,12-tris-(tert-butyl-dimethyl-silanyloxy)-14-hydroxy-5,7,9,11,13,15-hexamethyl-nonadeca-3,8,16,18-tetraenyl]-5,6-dihydro-pyran-2-one
• CAS: 835929-40-3
• 化学式: C₅₀H₉₄O₆Si₃
• 分子量: 875.549
• InChiKey: XCEJEGPUVQEQDI-SMFUWILOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.23
• 重原子数：
  59.0
• 可旋转键数：
  21.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  74.22
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (5R,6S)-3,5-Dimethyl-6-[(3Z,8Z,16Z)-(2S,5S,6S,7S,11S,12R,13R,14S,15S)-2,6,12-tris-(tert-butyl-dimethyl-silanyloxy)-14-hydroxy-5,7,9,11,13,15-hexamethyl-nonadeca-3,8,16,18-tetraenyl]-5,6-dihydro-pyran-2-one 在 盐酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 Propyl-carbamic acid (6Z,11Z)-(1S,2S,3R,4S,8S,9S,10S,13S)-14-((2S,3R)-3,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-3,9,13-trihydroxy-2,4,6,8,10-pentamethyl-1-((Z)-(S)-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
• 作为产物：
  描述：

  (5R,6S)-6-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-propyl]-3,5-dimethyl-5,6-dihydro-pyran-2-one 在 水 、 甲基锂 、 碳酸氢钠 、 戴斯-马丁氧化剂 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 lithium bromide 作用下， 以 四氢呋喃 、 二氯甲烷 、 正戊烷 为溶剂， 反应 6.75h， 生成 (5R,6S)-3,5-Dimethyl-6-[(3Z,8Z,16Z)-(2S,5S,6S,7S,11S,12R,13R,14S,15S)-2,6,12-tris-(tert-butyl-dimethyl-silanyloxy)-14-hydroxy-5,7,9,11,13,15-hexamethyl-nonadeca-3,8,16,18-tetraenyl]-5,6-dihydro-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