methyl 2,3,4-tri-O-benzyl-6-deoxy-6-methyl-α-D-galactopyranoside | 1092684-17-7

• 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-deoxy-6-methyl-α-D-galactopyranoside
• 英文别名: (2R,3S,4S,5R,6S)-2-ethyl-6-methoxy-3,4,5-tris(phenylmethoxy)oxane
• CAS: 1092684-17-7
• 化学式: C₂₉H₃₄O₅
• 分子量: 462.586
• InChiKey: JZDXCHCIXIQIHC-LLQHYSMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  34
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4-tri-O-benzyl-6-deoxy-6-methyl-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-deoxy-6-methyl-α-D-galactopyranose 、 2,3,4-tri-O-benzyl-6-deoxy-6-methyl-β-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：

  methyl 2,3,4-tri-O-benzyl-6,7-dideoxy-α-D-galacto-hept-6-enopyranoside 在 双氧水 、 一水合肼 作用下， 以 乙醇 、 水 为溶剂， 反应 21.0h， 以87%的产率得到methyl 2,3,4-tri-O-benzyl-6-deoxy-6-methyl-α-D-galactopyranoside
  参考文献：
  名称：

  NOVEL GLYCOLIPID AND USE THEREOF

  摘要：

  公开号：

  EP2272854B1

文献信息

• RCAI-61, the 6′-O-methylated analog of KRN7000: its synthesis and potent bioactivity for mouse lymphocytes to produce interferon-γ in vivo
  作者：Takuya Tashiro、Ryusuke Nakagawa、Sayo Inoue、Masao Shiozaki、Hiroshi Watarai、Masaru Taniguchi、Kenji Mori

  DOI：10.1016/j.tetlet.2008.09.074

  日期：2008.11

  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.