(2'S,3'S,4'R)-4,6-di-O-benzyl-2-O-(2'-N-benzylamino-3',4'-dihydroxyoctadecyl)-myo-inositol | 1191953-64-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2'S,3'S,4'R)-4,6-di-O-benzyl-2-O-(2'-N-benzylamino-3',4'-dihydroxyoctadecyl)-myo-inositol
• CAS: 1191953-64-6
• 化学式: C₄₅H₆₇NO₈
• 分子量: 750.029
• InChiKey: RFDYQPFPSPPOSW-VNKDATJPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.61
• 重原子数：
  54.0
• 可旋转键数：
  27.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  140.87
• 氢给体数：
  6.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (2'S,3'S,4'R)-4,6-di-O-benzyl-2-O-(2'-N-benzylamino-3',4'-dihydroxyoctadecyl)-myo-inositol 在 盐酸 、 palladium 10% on activated carbon 、 水 作用下， 以 甲醇 、 环己烯 为溶剂， 反应 8.0h， 生成 (1R,2S,3R,4R,5S,6s)-6-(((2S,3S,4R)-2-amino-3,4-dihydroxyoctadecyl)oxy)cyclohexane-1,2,3,4,5-pentaol
  参考文献：
  名称：

  RCAI-37, 56, 59, 60, 92, 101, and 102, cyclitol and carbasugar analogs of KRN7000: Their synthesis and bioactivity for mouse lymphocytes to produce Th1-biased cytokines

  摘要：

  Cyclitol [RCAI-37 (1), 59 (5), 92 (7), and 102 (2)] and carbasugar analogs [RCAI-56 (3), 60 (4), and 101 (6)] of KRN7000 were synthesized through coupling reactions of the corresponding cyclitol or carbasugar derivatives with a cyclic sulfamidate (9) as the key step. Bioassay showed RCAI-56 (3, carbagalactose analog of KRN7000), 59 (5, 1-deoxy-neo-inositol analog), and 92 (7, 1-O-methylated 5) to be remarkably potent stimulants of mouse lymphocytes to produce Th1-biased cytokines, such as interferon-c, in vivo. RCAI-60 (4, carbafucose analog) and RCAI-101 (6, 6-O-methylated 3) showed strong bioactivity, on the other hands, RCAI-37 (1, myo-inositol analog) and 102 (2, neo-inositol analog) induced little cytokine production. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.07.025
• 作为产物：
  描述：

  (2'S,3'S,4'R)-4,6-di-O-benzyl-2-O-(2'-N-benzylamino-3',4'-dihydroxy-3',4'-O-isopropylideneoctadecyl)-myo-inositol 1,3,5-orthoformate 在 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 8.0h， 以79%的产率得到(2'S,3'S,4'R)-4,6-di-O-benzyl-2-O-(2'-N-benzylamino-3',4'-dihydroxyoctadecyl)-myo-inositol
  参考文献：
  名称：

  RCAI-37, 56, 59, 60, 92, 101, and 102, cyclitol and carbasugar analogs of KRN7000: Their synthesis and bioactivity for mouse lymphocytes to produce Th1-biased cytokines

  摘要：

  Cyclitol [RCAI-37 (1), 59 (5), 92 (7), and 102 (2)] and carbasugar analogs [RCAI-56 (3), 60 (4), and 101 (6)] of KRN7000 were synthesized through coupling reactions of the corresponding cyclitol or carbasugar derivatives with a cyclic sulfamidate (9) as the key step. Bioassay showed RCAI-56 (3, carbagalactose analog of KRN7000), 59 (5, 1-deoxy-neo-inositol analog), and 92 (7, 1-O-methylated 5) to be remarkably potent stimulants of mouse lymphocytes to produce Th1-biased cytokines, such as interferon-c, in vivo. RCAI-60 (4, carbafucose analog) and RCAI-101 (6, 6-O-methylated 3) showed strong bioactivity, on the other hands, RCAI-37 (1, myo-inositol analog) and 102 (2, neo-inositol analog) induced little cytokine production. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.07.025