32-O-acetyl-ascomycin | 1180009-71-5

• 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: 32-O-acetyl-ascomycin
• 英文别名: [(1R,2R,4R)-4-[(E)-2-[(1R,9S,12S,13R,14S,17R,18E,21S,23S,24R,25S,27R)-17-ethyl-1,14-dihydroxy-23,25-dimethoxy-13,19,21,27-tetramethyl-2,3,10,16-tetraoxo-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacos-18-en-12-yl]prop-1-enyl]-2-methoxycyclohexyl] acetate
• CAS: 1180009-71-5
• 化学式: C₄₅H₇₁NO₁₃
• 分子量: 834.058
• InChiKey: LAGIHSBLLRADBT-JQJSDFSTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  59
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  184
• 氢给体数：
  2
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  32-O-acetyl-ascomycin 、 叔丁基二甲硅基三氟甲磺酸酯 在 2,6-二甲基吡啶 作用下， 以88%的产率得到24-O-tert-butyldimethylsilyl-32-O-acetyl-ascomycin
  参考文献：
  名称：

  First chemoenzymatic synthesis of immunomodulating macrolactam pimecrolimus

  摘要：

  The preparation of pimecrolimus, a synthetic derivative of ascomycin endowed with immunomodulatory activity, requires the selective protection of 24-hydroxy group of the ascomycin, before elaboration of the 32-hydroxy group. The aim was achieved by means of two regioselective Candida antarctica lipase-catalyzed steps. The structure of the new key intermediates, 24-, 32-monoacetates, and 24,32-diacetate, was established by means of an unambiguous NMR study. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.05.066
• 作为产物：
  描述：

  乙酸乙烯酯 、 长川霉素 在 Candida antarctica lipase 作用下， 以 甲苯 为溶剂， 反应 80.0h， 以94%的产率得到32-O-acetyl-ascomycin
  参考文献：
  名称：

  First chemoenzymatic synthesis of immunomodulating macrolactam pimecrolimus

  摘要：

  The preparation of pimecrolimus, a synthetic derivative of ascomycin endowed with immunomodulatory activity, requires the selective protection of 24-hydroxy group of the ascomycin, before elaboration of the 32-hydroxy group. The aim was achieved by means of two regioselective Candida antarctica lipase-catalyzed steps. The structure of the new key intermediates, 24-, 32-monoacetates, and 24,32-diacetate, was established by means of an unambiguous NMR study. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.05.066