6-(1-hydroxy-19,30-dimethoxy-15,17,21,23,29,35-hexamethyl-2,3,10,14,20-pentaoxo-18-triethylsilanyloxy-11,36-dioxa-4-aza-tricyclo[30.3.1.04,9]hexatriaconta-16,24,26,28-tetraen-12-yl)-4-(2-hydroxy-ethyl)-heptanoic acid methyl ester | 223916-28-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯内酰胺
• 英文名称: 6-(1-hydroxy-19,30-dimethoxy-15,17,21,23,29,35-hexamethyl-2,3,10,14,20-pentaoxo-18-triethylsilanyloxy-11,36-dioxa-4-aza-tricyclo[30.3.1.04,9]hexatriaconta-16,24,26,28-tetraen-12-yl)-4-(2-hydroxy-ethyl)-heptanoic acid methyl ester
• CAS: 223916-28-7
• 化学式: C₅₇H₉₃NO₁₄Si
• 分子量: 1044.45
• InChiKey: SHWTZWRHIMTBGX-AIICCZFXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.99
• 重原子数：
  73.0
• 可旋转键数：
  15.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  201.5
• 氢给体数：
  2.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  6-(1-hydroxy-19,30-dimethoxy-15,17,21,23,29,35-hexamethyl-2,3,10,14,20-pentaoxo-18-triethylsilanyloxy-11,36-dioxa-4-aza-tricyclo[30.3.1.04,9]hexatriaconta-16,24,26,28-tetraen-12-yl)-4-(2-hydroxy-ethyl)-heptanoic acid methyl ester 在 吡啶 、 氢氟酸 作用下， 以 乙腈 为溶剂， 反应 3.0h， 生成 methyl (4S,6R)-6-[(1R,9S,12S,15R,16E,18R,19R,21R,23S,24E,26E,28E,30S,32S,35R)-1,18-dihydroxy-19,30-dimethoxy-15,17,21,23,29,35-hexamethyl-2,3,10,14,20-pentaoxo-11,36-dioxa-4-azatricyclo[30.3.1.04,9]hexatriaconta-16,24,26,28-tetraen-12-yl]-4-(2-hydroxyethyl)heptanoate
  参考文献：
  名称：

  Cleavage of the cyclohexyl-subunit of rapamycin results in loss of immunosuppressive activity

  摘要：

  The cyclohexyl-subunit of rapamycin was cleaved by a sequence involving a Baeyer-Villiger reaction and acid hydrolysis of the resulting lactone-acetal as key steps. Binding of this new rapamycin derivative to FKBP12 was only slightly reduced by this modification, whereas the loss of antiproliferative and immunosuppressive activity was dramatic. These findings indicate that part of the cyclohexyl-subunit of rapamycin could belong to its effector domain. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00007-4
• 作为产物：
  描述：

  雷帕霉素 在 四氢呋喃 、 咪唑 、 草酰氯 、 水 、 L-Selectride 、 碳酸氢钠 、 溶剂黄146 、 二甲基亚砜 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 6.42h， 生成 6-(1-hydroxy-19,30-dimethoxy-15,17,21,23,29,35-hexamethyl-2,3,10,14,20-pentaoxo-18-triethylsilanyloxy-11,36-dioxa-4-aza-tricyclo[30.3.1.04,9]hexatriaconta-16,24,26,28-tetraen-12-yl)-4-(2-hydroxy-ethyl)-heptanoic acid methyl ester
  参考文献：
  名称：

  Cleavage of the cyclohexyl-subunit of rapamycin results in loss of immunosuppressive activity

  摘要：

  The cyclohexyl-subunit of rapamycin was cleaved by a sequence involving a Baeyer-Villiger reaction and acid hydrolysis of the resulting lactone-acetal as key steps. Binding of this new rapamycin derivative to FKBP12 was only slightly reduced by this modification, whereas the loss of antiproliferative and immunosuppressive activity was dramatic. These findings indicate that part of the cyclohexyl-subunit of rapamycin could belong to its effector domain. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00007-4