methyl 2-O-benzoyl-4,6-O-benzylidene-3-deoxy-α-D-galctopyranoside | 1186196-12-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: methyl 2-O-benzoyl-4,6-O-benzylidene-3-deoxy-α-D-galctopyranoside
• CAS: 1186196-12-2
• 化学式: C₂₁H₂₂O₆
• 分子量: 370.402
• InChiKey: ZVISFSHNPBCDIT-OMEDHOOWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.09
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  63.22
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl 2-O-benzoyl-4,6-O-benzylidene-3-deoxy-α-D-galctopyranoside 在 甲醇 、 水 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以97%的产率得到methyl 4,6-O-benzylidene-3-deoxy-α-D-xylo-hexopyranoside
  参考文献：
  名称：

  Synthesis and evaluation of 3″- and 4″-deoxy and -fluoro analogs of the immunostimulatory glycolipid, KRN7000

  摘要：

  Four 3 ''- and 4 ''-deoxy and -fluorogalactosyl ceramides were synthesized, and their ability to stimulate iNKT cells, based on levels of IL-2 production, was assessed in three NKT cell receptor hybridomas. In two of the hybridomas, 1.2 and 2H4, all of the analogs were immunostimulatory, while in the 1.4 hybridoma only the 4 ''-fluoro analog led to the production of significant levels of IL-2. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.06.005
• 作为产物：
  描述：

  methyl 2-O-benzoyl-4,6-O-benzylidene-3-O-phenoxythiocarbonyl-α-D-galactopyranoside 在 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 20.0h， 以84%的产率得到methyl 2-O-benzoyl-4,6-O-benzylidene-3-deoxy-α-D-galctopyranoside
  参考文献：
  名称：

  Synthesis and evaluation of 3″- and 4″-deoxy and -fluoro analogs of the immunostimulatory glycolipid, KRN7000

  摘要：

  Four 3 ''- and 4 ''-deoxy and -fluorogalactosyl ceramides were synthesized, and their ability to stimulate iNKT cells, based on levels of IL-2 production, was assessed in three NKT cell receptor hybridomas. In two of the hybridomas, 1.2 and 2H4, all of the analogs were immunostimulatory, while in the 1.4 hybridoma only the 4 ''-fluoro analog led to the production of significant levels of IL-2. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.06.005