2,3,4-tri-O-benzyl-6-O-propyl-D-galactopyranosyl fluoride | 1092684-25-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,3,4-tri-O-benzyl-6-O-propyl-D-galactopyranosyl fluoride
• CAS: 1092684-25-7
• 化学式: C₃₀H₃₅FO₅
• 分子量: 494.603
• InChiKey: KUPRVCIKLMXIMF-LSZMOXLZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.86
• 重原子数：
  36.0
• 可旋转键数：
  13.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  46.15
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-benzyl-6-O-propyl-D-galactopyranosyl fluoride 、 (2S,3S,4R)-3,4-二[(叔-丁基二甲基硅烷基)氧基]-2-二十六烷酰基氨基-4-十八烷醇 在 silver perchlorate 、 tin(ll) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成
  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：

  2,3,4-tri-O-benzyl-6-O-propyl-D-galactopyranose 在 二乙胺基三氟化硫 作用下， 以 二氯甲烷 为溶剂， 反应 0.67h， 以96%的产率得到2,3,4-tri-O-benzyl-6-O-propyl-D-galactopyranosyl fluoride
  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