2,3,4-tri-O-benzyl-6-O-methyl-β-D-galactopyranose | 1435264-89-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4-tri-O-benzyl-6-O-methyl-β-D-galactopyranose
• 英文别名: (2R,3R,4S,5S,6R)-6-(methoxymethyl)-3,4,5-tris(phenylmethoxy)oxan-2-ol
• CAS: 1435264-89-3
• 化学式: C₂₈H₃₂O₆
• 分子量: 464.558
• InChiKey: FLJUYHZJTGMKJJ-QBROEMLDSA-N

物化性质

• 沸点：
  599.3±50.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  34
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2,3,4-tri-O-benzyl-6-O-methyl-α-D-galactopyranose 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 2,3,4-tri-O-benzyl-6-O-methyl-α-D-galactopyranose 、 2,3,4-tri-O-benzyl-6-O-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