phenyl 3-deoxy-3-fluoro-2,4,6-tri-O-benzyl-1-thio-β-D-galactopyranoside | 1186196-09-7

• 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: phenyl 3-deoxy-3-fluoro-2,4,6-tri-O-benzyl-1-thio-β-D-galactopyranoside
• CAS: 1186196-09-7
• 化学式: C₃₃H₃₃FO₄S
• 分子量: 544.687
• InChiKey: QQNUXCSSNQKMSI-CYEGLCQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.23
• 重原子数：
  39.0
• 可旋转键数：
  12.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2S,3R)-3-O-benzyl-2-(N-hexacosanoylamino)octadecan-1,3-diol 、 phenyl 3-deoxy-3-fluoro-2,4,6-tri-O-benzyl-1-thio-β-D-galactopyranoside 在 N-碘代丁二酰亚胺 、 silver trifluoromethanesulfonate 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 4.0h， 以47%的产率得到(2S,3R)-3-benzyloxy-1-(3''-deoxy-3''-fluoro-2'',4'',6''-tri-O-benzyl-α-D-galactopyranosyl)-2-(N-hexacosanoyloamino)octadecane
  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：

  phenyl 3-deoxy-3-fluoro-1-thio-β-D-galactopyranoside 、 溴甲苯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 以69%的产率得到phenyl 3-deoxy-3-fluoro-2,4,6-tri-O-benzyl-1-thio-β-D-galactopyranoside
  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