phenyl 3,4-O-isopropylidene-6-O-tert-butyldiphenylsilyl-2-O-(5-azidopentyl)-1-thio-β-D-galactopyranoside | 1224436-71-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 3,4-O-isopropylidene-6-O-tert-butyldiphenylsilyl-2-O-(5-azidopentyl)-1-thio-β-D-galactopyranoside
• CAS: 1224436-71-8
• 化学式: C₃₆H₄₇N₃O₅SSi
• 分子量: 661.938
• InChiKey: NJURFJFTNAJXLM-YODGASFJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.47
• 重原子数：
  46.0
• 可旋转键数：
  14.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  94.91
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  phenyl 3,4-O-isopropylidene-6-O-tert-butyldiphenylsilyl-2-O-(5-azidopentyl)-1-thio-β-D-galactopyranoside 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  Synthesis of a Novel α-Galactosyl Ceramide Haptenated-Lipid Antigen, a Useful Tool in Demonstrating the Involvement of iNKT Cells in the Production of Antilipid Antibodies

  摘要：

  A new haptenated derivative of a-galactosyl ceramide (alpha-GalCer) has been synthesized to assist in the study of the mechanism of T cell help for the production of B cell antibodies. Our synthetic route provides access to an amine intermediate which can easily be extended to generate an array of compounds, useful in various ongoing studies. Herein, we also describe the biological evaluation of the nitrophenyl (NP) haptenated alpha-GalCer and demonstrate its importance in such mechanistic studies. For instance, ill vitro studies showed that NP-alpha-GalCer stimulates both T and B cell proliferation while in vivo studies in immunized mice showed the production of IgG anti-NP antibodies after exposure to NP-alpha-GalCer. The interpretation of these results helps toward a better understanding of T cell help for the production of antibodies.

  DOI：

  10.1021/bc9005255
• 作为产物：
  描述：

  (((3aS,4R,6S,7R,7aS)-7-((5-bromopentyl)oxy)-2,2-dimethyl-6-(phenylthio)tetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-4-yl)methoxy)(tert-butyl)diphenylsilane 在 sodium azide 作用下， 以 二甲基亚砜 为溶剂， 以1.8 g的产率得到phenyl 3,4-O-isopropylidene-6-O-tert-butyldiphenylsilyl-2-O-(5-azidopentyl)-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of a Novel α-Galactosyl Ceramide Haptenated-Lipid Antigen, a Useful Tool in Demonstrating the Involvement of iNKT Cells in the Production of Antilipid Antibodies

  摘要：

  A new haptenated derivative of a-galactosyl ceramide (alpha-GalCer) has been synthesized to assist in the study of the mechanism of T cell help for the production of B cell antibodies. Our synthetic route provides access to an amine intermediate which can easily be extended to generate an array of compounds, useful in various ongoing studies. Herein, we also describe the biological evaluation of the nitrophenyl (NP) haptenated alpha-GalCer and demonstrate its importance in such mechanistic studies. For instance, ill vitro studies showed that NP-alpha-GalCer stimulates both T and B cell proliferation while in vivo studies in immunized mice showed the production of IgG anti-NP antibodies after exposure to NP-alpha-GalCer. The interpretation of these results helps toward a better understanding of T cell help for the production of antibodies.

  DOI：

  10.1021/bc9005255