(2'S,3'S,4'R)-1D-(1,2,3/4,5)-2,3,4-tri-O-benzyl-5-O-(2'-N-benzylamino-3',4'-dihydroxy-3',4'-O-isopropylideneoctadecyl)-1-O-methylcyclohexanepentol | 1191953-84-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2'S,3'S,4'R)-1D-(1,2,3/4,5)-2,3,4-tri-O-benzyl-5-O-(2'-N-benzylamino-3',4'-dihydroxy-3',4'-O-isopropylideneoctadecyl)-1-O-methylcyclohexanepentol
• CAS: 1191953-84-0
• 化学式: C₅₆H₇₉NO₇
• 分子量: 878.246
• InChiKey: PXAGHZWACOWHIO-XUDSWWKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.32
• 重原子数：
  64.0
• 可旋转键数：
  30.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  76.64
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (2'S,3'S,4'R)-1D-(1,2,3/4,5)-2,3,4-tri-O-benzyl-5-O-(2'-N-benzylamino-3',4'-dihydroxy-3',4'-O-isopropylideneoctadecyl)-1-O-methylcyclohexanepentol 在 盐酸 、 水 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以85%的产率得到(2'S,3'S,4'R)-1D-(1,2,3/4,5)-2,3,4-tri-O-benzyl-5-O-(2'-N-benzylamino-3',4'-dihydroxyoctadecyl)-1-O-methylcyclohexanepentol
  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：

  1D-(1,2,3/4,5)-2,3,4-tri-O-benzyl-1-O-methylcyclohexanepentol 、 (S)-3-Benzyl-4-((4S,5R)-2,2-dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-[1,2,3]oxathiazolidine 2,2-dioxide 在 sodium hydride 、 硫酸 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 mineral oil 、 乙醚 、 水 为溶剂， 反应 1.33h， 以87%的产率得到(2'S,3'S,4'R)-1D-(1,2,3/4,5)-2,3,4-tri-O-benzyl-5-O-(2'-N-benzylamino-3',4'-dihydroxy-3',4'-O-isopropylideneoctadecyl)-1-O-methylcyclohexanepentol
  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