(2S,3S,4R)-1-O-(5a-carba-α-D-fucopyranosyl)-2-hexacosanoylaminooctadecane-1,3,4-triol | 1050218-72-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,4R)-1-O-(5a-carba-α-D-fucopyranosyl)-2-hexacosanoylaminooctadecane-1,3,4-triol
• 英文别名: RCA-60；(2S,3S,4R)-1-(5a-carba-α-D-fucopyranosyloxy)-2-(hexacosanoylamino)-3,4-octadecanediol；N-[(2S,3S,4R)-3,4-dihydroxy-1-[(1S,2R,3S,4S,5S)-2,3,4-trihydroxy-5-methylcyclohexyl]oxyoctadecan-2-yl]hexacosanamide
• CAS: 1050218-72-8
• 化学式: C₅₁H₁₀₁NO₇
• 分子量: 840.365
• InChiKey: KNCMSHBFXXHBMF-VBDPUHEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17.3
• 重原子数：
  59
• 可旋转键数：
  43
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.98
• 拓扑面积：
  140
• 氢给体数：
  6
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  hexacosanoyl chloride 、 (1S,2S,3R,4S,6S)-4-(((2S,3S,4R)-2-amino-3,4-dihydroxyoctadecyl)oxy)-6-methylcyclohexane-1,2,3-triol 在 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 为溶剂， 反应 19.0h， 以19%的产率得到(2S,3S,4R)-1-O-(5a-carba-α-D-fucopyranosyl)-2-hexacosanoylaminooctadecane-1,3,4-triol
  参考文献：
  名称：

  NOVEL PSEUDOGLYCOLIPID AND USE THEREOF

  摘要：

  公开号：

  EP2133326B1

文献信息

• NOVEL PSEUDOGLYCOLIPID AND USE THEREOF
  申请人：Riken

  公开号：EP2133326B1

  公开（公告）日：2015-12-23
• 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
  作者：Takuya Tashiro、Ryusuke Nakagawa、Takatsugu Hirokawa、Sayo Inoue、Hiroshi Watarai、Masaru Taniguchi、Kenji Mori

  DOI：10.1016/j.bmc.2009.07.025

  日期：2009.9

  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.