2-(trimethylsilil)ethyl 2-deoxy-4-O-diphenylphosphono-3-O-[(R)-3-tetradecanoyloxytetradecanoyl]-6-O-(2,2,2-trichloro-1,1-dimethylethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside | 216013-12-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: 2-(trimethylsilil)ethyl 2-deoxy-4-O-diphenylphosphono-3-O-[(R)-3-tetradecanoyloxytetradecanoyl]-6-O-(2,2,2-trichloro-1,1-dimethylethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside
• 英文别名: 2-(trimethylsilyl)ethyl 2-deoxy-4-O-diphenylphosphono-3-O-[(R)-3-tetradecanoyloxytetradecanoyl]-6-O-(2,2,2-trichloro-1,1-dimethylethoxycarbonyl)-2-(2,2,2-trichlorethoxycarbonylamino)-β-D-glucopyranoside；2-(Trimethylsilyl)ethyl 2-deoxy-4-o-diphenylphosphono-3-o-[(r)-3-tetradecanoyloxytetradecanoyl]-6-o-(2,2,2-trichloro-1,1-dimethylethoxycarbonyl)-2-(2,2,2-trichlorethoxycarbonylamino)-beta-d-glucopyranoside；[(2R,3S,4R,5R,6R)-3-diphenoxyphosphoryloxy-5-(2,2,2-trichloroethoxycarbonylamino)-2-[(1,1,1-trichloro-2-methylpropan-2-yl)oxycarbonyloxymethyl]-6-(2-trimethylsilylethoxy)oxan-4-yl] (3R)-3-tetradecanoyloxytetradecanoate
• CAS: 216013-12-6
• 化学式: C₅₉H₉₂Cl₆NO₁₅PSi
• 分子量: 1327.15
• InChiKey: JBMPRKOJTBLGGP-SFLGFWQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  18.32
• 重原子数：
  83
• 可旋转键数：
  46
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  190
• 氢给体数：
  1
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  2-(trimethylsilil)ethyl 2-deoxy-4-O-diphenylphosphono-3-O-[(R)-3-tetradecanoyloxytetradecanoyl]-6-O-(2,2,2-trichloro-1,1-dimethylethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside 在 1,1-二氯甲醚 、 zinc(II) chloride 作用下， 以 氯仿 为溶剂， 以88%的产率得到2-deoxy-4-O-diphenylphosphono-3-O-[(R)-3-tetradecanoyloxytetradecanoyl]-6-O-(2,2,2-trichloro-1,1-dimethylethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl chloride
  参考文献：
  名称：

  Chemical Synthesis of the Major Constituents ofSalmonella MinnesotaMonophosphoryl Lipid A

  摘要：

  DOI：

  10.1080/07328309808002363
• 作为产物：
  描述：

  (R)-3-(dodecanoyloxy)tetradecanoic acid 在 吡啶 、 二甲基氨基丙基乙基碳酰胺 、 4-吡咯烷基吡啶 、 溶剂黄146 、 二异丙胺 作用下， 以 二氯甲烷 为溶剂， 反应 8.5h， 生成 2-(trimethylsilil)ethyl 2-deoxy-4-O-diphenylphosphono-3-O-[(R)-3-tetradecanoyloxytetradecanoyl]-6-O-(2,2,2-trichloro-1,1-dimethylethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside
  参考文献：
  名称：

  Chemical Synthesis of the Major Constituents ofSalmonella MinnesotaMonophosphoryl Lipid A

  摘要：

  DOI：

  10.1080/07328309808002363
• 作为试剂：
  描述：

  2-(trimethylsilil)ethyl 2-deoxy-3-O-[(R)-3-tetradecanoyloxytetradecanoyl]-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside 、 吡啶 、 2,2,2-三氯-1,1-二甲基乙基氯甲酸酯 、 4-吡咯烷基吡啶 、 N,N-二异丙基乙胺 、 氯磷酸二苯酯 在 盐酸 、 水 、 碳酸氢钠 、 Sodium sulfate-III 、 silica gel 、 EtOAc-hexanes 、 2-(trimethylsilil)ethyl 2-deoxy-4-O-diphenylphosphono-3-O-[(R)-3-tetradecanoyloxytetradecanoyl]-6-O-(2,2,2-trichloro-1,1-dimethylethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside 作用下， 以 二氯甲烷 为溶剂， 反应 8.75h， 以to give 15.1 g (95%) of 2-(trimethylsilyl)ethyl 2-deoxy-4-O-diphenylphosphono-3-O-[(R)-3-tetradecanoyloxytetradecanoyl]-6-O-(2,2,2-trichloro-1,1-dimethylethoxycarbonyl)-2-(2,2,2-trichlorethoxycarbonylamino)-β-D-glucopyranoside (compound 8) as a viscous oil的产率得到2-(trimethylsilil)ethyl 2-deoxy-4-O-diphenylphosphono-3-O-[(R)-3-tetradecanoyloxytetradecanoyl]-6-O-(2,2,2-trichloro-1,1-dimethylethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside
  参考文献：
  名称：

  Phosphoglycolipid and methods for its use

  摘要：

  本发明涉及一种新型的磷酸甘油脂化合物。该发明的化合物是2-去氧-6-O-［2-去氧-4-O-磷酸-3-O-［(R)-3-十四烷氧基-十四烷酰基］-2-［(R)-3-十八烷氧基-十四烷酰胺］-β-D-葡萄糖苷］-2-［(R)-3-十六烷氧基-十四烷酰胺］-D-葡萄糖苷及其药学上可接受的盐。该化合物不具有免疫反应性，不具有热原性，不具有毒性，但在缓解因缺血/再灌注损伤引起的组织损伤方面具有活性。本发明还公开了使用该化合物保护免受缺血/再灌注损伤引起的可逆和不可逆损伤的方法。

  公开号：

  US20020013291A1

文献信息

• Aminoalkyl glucosamine phosphate compounds and their use as adjuvants and immunoeffectors
  申请人：Corixa Corporation

  公开号：US06355257B1

  公开（公告）日：2002-03-12

  Aminoalkyl glucosamine phosphate compounds that are adjuvants and immunoeffectors are described and claimed. The compounds have a 2-deoxy-2-amino glucose in glycosidic linkage with an aminoalkyl (aglycon) group. Compounds are phosphorylated at the 4 or 6 carbon on the glucosamine ring and comprise three 3-alkanoyloxyalkanoyl residues. The compounds augment antibody production in immunized animals as well as stimulate cytokine production and activate macrophages. Methods for using the compounds as adjuvants and immunoeffectors are also disclosed.

  描述和声明了一种氨基糖胺磷酸盐化合物，它们是辅助剂和免疫效应物质。这些化合物具有一个2-脱氧-2-氨基葡萄糖与一个氨基烷基（非糖部分）基团的糖苷键连接。这些化合物在葡萄糖胺环上的4或6碳上磷酸化，并包括三个3-烷酰氧烷酰残基。这些化合物增强了免疫动物中的抗体产生，同时刺激细胞因子的产生并激活巨噬细胞。还公开了将这些化合物用作辅助剂和免疫效应物质的方法。
• Chemical Synthesis of the Major Constituents of<i>Salmonella Minnesota</i>Monophosphoryl Lipid A
  作者：David A. Johnson、C. Gregory Sowell、David S. Keegan、Mark T. Livesay

  DOI：10.1080/07328309808002363

  日期：1998.12
• 3-<i>O</i>-Desacyl Monophosphoryl Lipid A Derivatives:  Synthesis and Immunostimulant Activities
  作者：David A. Johnson、David S. Keegan、C. Gregory Sowell、Mark T. Livesay、Craig L. Johnson、Lara M. Taubner、Annalivia Harris、Kent R. Myers、Jennifer D. Thompson、Gary L. Gustafson、Michael J. Rhodes、J. Terry Ulrich、Jon R. Ward、Yvonne M. Yorgensen、John L. Cantrell、Valerie G. Brookshire

  DOI：10.1021/jm990222b

  日期：1999.11.1

  The synthesis of a series of novel analogues of lipid A, the active principle of lipopolysaccharide, is reported. In these compounds, the 1-O-phosphono and (R)-3-hydroxytetradecanoyl moieties of native Salmonella minnesota R595 lipid A have been replaced with hydrogen and the length of the normal fatty acyl residues has been systematically varied. Normal fatty acid chain length in the 3-O-desacyl monophosphoryl lipid A (MLS) series is shown to be a critical determinant of iNOS gene expression in activated mouse macrophages and the induction of proinflammatory cytokines in human peripheral monocytes. Examination of pyrogenicity in rabbits and lethal toxicity in D-galactosamine-treated mice shows that toxic effects in the MLA series can be ameliorated by modifying fatty acid chain length. When used as an adjuvant for tetanus toroid vaccines, certain MLA derivatives enhance the production of tetanus toroid-specific antibodies in mice.
• Phosphoglycolipid and methods for its use
  申请人：——

  公开号：US20020013291A1

  公开（公告）日：2002-01-31

  The invention concerns a novel phosphoglycoilpid compound. The compound of the subject invention is 2-Deoxy-6-O-[2-deoxy-4-O-phosphono-3-O-[(R)-3-tetradecanoyloxytetradecanoyl]-2-[(R)-3-octadecanoyloxytetradecanoylamino]-&bgr;-D-glucopyranosyl]-2-[(R)-3-hexadecanoyloxytetradecanoylamino]-D-glucopyranose and pharmaceutically acceptable salts thereof. The compound is not immunoreactive, not pyrogenic, not toxic but is active in ameliorating tissue damage due to ischemia/reperfusion injury. Methods for using the subject compound to protect against reversible and irreversible damage due to ischemia/reperfusion injury are also disclosed.

  本发明涉及一种新型的磷酸甘油脂化合物。该发明的化合物是2-去氧-6-O-［2-去氧-4-O-磷酸-3-O-［(R)-3-十四烷氧基-十四烷酰基］-2-［(R)-3-十八烷氧基-十四烷酰胺］-β-D-葡萄糖苷］-2-［(R)-3-十六烷氧基-十四烷酰胺］-D-葡萄糖苷及其药学上可接受的盐。该化合物不具有免疫反应性，不具有热原性，不具有毒性，但在缓解因缺血/再灌注损伤引起的组织损伤方面具有活性。本发明还公开了使用该化合物保护免受缺血/再灌注损伤引起的可逆和不可逆损伤的方法。