(2S,3R)-3-benzyloxy-2-(N-tert-butyloxycarbonylamino)-1-(2'',3'',6''-tri-O-benzyl-4''-deoxy-β-D-galactopyranosyl)octadecane | 1186196-17-7

• 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: (2S,3R)-3-benzyloxy-2-(N-tert-butyloxycarbonylamino)-1-(2'',3'',6''-tri-O-benzyl-4''-deoxy-β-D-galactopyranosyl)octadecane
• CAS: 1186196-17-7
• 化学式: C₅₇H₈₁NO₈
• 分子量: 908.272
• InChiKey: JYZQGUVTZQHMCZ-WZOHZWNASA-N

物化性质

• 沸点：
  896.7±65.0 °C(predicted)
• 密度：
  1.09±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  13.47
• 重原子数：
  66.0
• 可旋转键数：
  32.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  93.71
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (2S,3R)-3-benzyloxy-2-(N-tert-butyloxycarbonylamino)-1-(2'',3'',6''-tri-O-benzyl-4''-deoxy-β-D-galactopyranosyl)octadecane 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以81%的产率得到(2S,3R)-3-benzyloxy-1-(2'',3'',6''-tri-O-benzyl-4''-deoxy-α-D-galactopyranosyl)-2-aminooctadecane
  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：

  (2S,4R)-2-(N-tert-butoxycarbonyl)amino-3-benzyloxyoctadecan-1-ol 、 phenyl 2,3,6-tri-O-benzyl-4-deoxy-1-thio-β-D-xylo-hexopyranoside 在 N-碘代丁二酰亚胺 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 以30%的产率得到(2S,3R)-3-benzyloxy-2-(N-tert-butyloxycarbonylamino)-1-(2'',3'',6''-tri-O-benzyl-4''-deoxy-β-D-galactopyranosyl)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