p-methylphenyl 2-O-benzyl-4,6-O-benzylidene-3-O-levulinoyl-1-thio-D-galactopyranoside | 896444-12-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-methylphenyl 2-O-benzyl-4,6-O-benzylidene-3-O-levulinoyl-1-thio-D-galactopyranoside
• CAS: 896444-12-5
• 化学式: C₃₂H₃₄O₇S
• 分子量: 562.684
• InChiKey: YMLIMDPNFHOCIG-SOFYQYIMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.79
• 重原子数：
  40.0
• 可旋转键数：
  10.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  80.29
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  p-methylphenyl 2-O-benzyl-4,6-O-benzylidene-3-O-levulinoyl-1-thio-D-galactopyranoside 在 钯 吡啶 、 sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 pyridine-SO3 complex 、 三氟甲磺酸三甲基硅酯 、 3 A molecular sieve 、 氢气 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 丙酮 、 甲苯 为溶剂， 反应 32.17h， 生成 2-hexacosylamino-1-O-(3-O-sulfo-α-D-galactopyranosyl)-D-ribo-1,3,4-octadecanetriol sodium salt
  参考文献：
  名称：

  Synthesis and human NKT cell stimulating properties of 3-O-sulfo-α/β-galactosylceramides

  摘要：

  Two novel hybrid molecules 3-O-sulfo-alpha/beta-galactosylceramide 3 and 4, which are derived from an immunostimulatory agent alpha-GalCer 1 and self-glycolipid ligand sulfatide 2, were designed and synthesized. Compound 3 was shown to efficiently stimulate human NKT cells to secret IL-4 and IFN-gamma, with activities similar to 1, suggesting that modification of the 3"-OH position of the galactose moiety with sulfate has no significant effect on NKT cell stimulation. As a comparison, the beta-isomer 4 has no affinity to NKT cells, which demonstrates that the alpha-glycosidic bond of galactosylceramide is crucial to the NKT cells activation. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.02.018
• 作为产物：
  描述：

  、 乙酰丙酸 在 4-二甲氨基吡啶 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以78%的产率得到p-methylphenyl 2-O-benzyl-4,6-O-benzylidene-3-O-levulinoyl-1-thio-D-galactopyranoside
  参考文献：
  名称：

  Synthesis and human NKT cell stimulating properties of 3-O-sulfo-α/β-galactosylceramides

  摘要：

  Two novel hybrid molecules 3-O-sulfo-alpha/beta-galactosylceramide 3 and 4, which are derived from an immunostimulatory agent alpha-GalCer 1 and self-glycolipid ligand sulfatide 2, were designed and synthesized. Compound 3 was shown to efficiently stimulate human NKT cells to secret IL-4 and IFN-gamma, with activities similar to 1, suggesting that modification of the 3"-OH position of the galactose moiety with sulfate has no significant effect on NKT cell stimulation. As a comparison, the beta-isomer 4 has no affinity to NKT cells, which demonstrates that the alpha-glycosidic bond of galactosylceramide is crucial to the NKT cells activation. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.02.018