methyl 2,3,4-tri-O-benzyl-6-O-ethyl-α-D-galactopyranoside | 1092684-15-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,4-tri-O-benzyl-6-O-ethyl-α-D-galactopyranoside
• 英文别名: (2R,3S,4S,5R,6S)-2-(ethoxymethyl)-6-methoxy-3,4,5-tris(phenylmethoxy)oxane
• CAS: 1092684-15-5
• 化学式: C₃₀H₃₆O₆
• 分子量: 492.612
• InChiKey: CMTHMNJUICSWHX-QBHLCAJUSA-N

物化性质

• 沸点：
  593.2±50.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  36
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4-tri-O-benzyl-6-O-ethyl-α-D-galactopyranoside 在 硫酸 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.83h， 生成 2,3,4-tri-O-benzyl-6-O-ethyl-D-galactopyranose
  参考文献：
  名称：

  RCAI-61 and related 6′-modified analogs of KRN7000: Their synthesis and bioactivity for mouse lymphocytes to produce interferon-γ in vivo

  摘要：

  We synthesized ten new analogs of 6'-modified KRN7000 (A): RCAI-58, 61, 64, 83, 85-87, 113, 119, and 125. They could be synthesized by alpha-selective galactosylation of ceramide 9 with the 6-modified D-galactopyranosyl fluorides (8a-8f) or L-arabinopyranosyl fluoride (17), or by etherification of the known alcohol 19. Bioassay of the ten analogs demonstrated that RCAI-61 (1, 6'-O-methylated analog of A) was the most potent immunostimulant among them, and could induce the production of a large amount of IFN-gamma even at a low concentration in mice in vivo. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.03.028
• 作为产物：
  描述：

  溴乙烷 、 methyl 2,3,4-tri-O-benzyl-α-D-galactopyranoside 在 四丁基碘化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 以98%的产率得到methyl 2,3,4-tri-O-benzyl-6-O-ethyl-α-D-galactopyranoside
  参考文献：
  名称：

  RCAI-61, the 6′-O-methylated analog of KRN7000: its synthesis and potent bioactivity for mouse lymphocytes to produce interferon-γ in vivo

  摘要：

  RCAI-61, the 6'-O-methylated analog of KRN7000, and six other analogs with modified 6'-position of the galactose moiety of KRN7000 were synthesized to examine their bioactivity for mouse lymphocytes. Methyl alpha-D-galactopyranoside was the starting material for RCAI-58, 61, 64, 83, 85, and 86, while RCAI-87 was prepared from methyl beta-L-arabinopyranoside. Bioassay showed RCAI-61 to be a Much more potent stimulant of mouse lymphocytes than KRN7000 and RCAI-56 to induce the production of a large amount of IFN-gamma in vivo. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.09.074

文献信息

• NOVEL GLYCOLIPID AND USE THEREOF
  申请人：Riken

  公开号：EP2272854B1

  公开（公告）日：2015-08-05