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 | 216014-59-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: 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
• 英文别名: 2-Deoxy-4-o-diphenylphosphono-3-o-[(r)-3-tetradecanoyloxytetradecanoyl]-6-o-(2,2,2-trichloro-1,1-dimethylethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-alpha-d-glucopyranosyl chloride；[(2R,3R,4R,5S,6R)-2-chloro-5-diphenoxyphosphoryloxy-3-(2,2,2-trichloroethoxycarbonylamino)-6-[(1,1,1-trichloro-2-methylpropan-2-yl)oxycarbonyloxymethyl]oxan-4-yl] (3R)-3-tetradecanoyloxytetradecanoate
• CAS: 216014-59-4
• 化学式: C₅₄H₇₉Cl₇NO₁₄P
• 分子量: 1245.36
• InChiKey: AWZGKYRPCTWGRK-OUQQSMASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  19.7
• 重原子数：
  77
• 可旋转键数：
  42
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  180
• 氢给体数：
  1
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  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 、 2-[(R)-3-tetradecanoyloxytetradecanoylamino]ethanol 在 4 A molecular sieve 、 silver trifluoromethanesulfonate 作用下， 以 1,2-二氯乙烷 为溶剂， 生成 2-[(R)-3-tetradecanoyloxytetradecanoylamino]ethyl 2-deoxy-4-O-diphenylphosphono-3-O-[(R)-3-tetradecanoyoxytetradecanoyl]-6-O-(2,2,2-trichloro-1,1-dimethylethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis and biological evaluation of a new class of vaccine adjuvants: aminoalkyl glucosaminide 4-phosphates (AGPs)

  摘要：

  A novel series of acylated omega-aminoalkyl 2-amino-2-deoxy-4-phosphono-beta-D-glucopyranosides (aminoalkyl glucosaminide 4-phosphates) was synthesized and screened for immunostimulant activity. Several of these compounds enhance the production of tetanus toroid-specific antibodies in mice and augment vaccine-induced cytotoxic T cells against EG.7-ova target cells. (C) 1999 Elsevier Science Ltd. Pill rights reserved.

  DOI：

  10.1016/s0960-894x(99)00374-1
• 作为产物：
  描述：

  (R)-3-(dodecanoyloxy)tetradecanoic acid 在 吡啶 、 1,1-二氯甲醚 、 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 、 zinc(II) chloride 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 8.5h， 生成 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
• 作为试剂：
  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 、 1,1-二氯甲醚 在 氯化锌 碳酸氢钠 、 Sodium sulfate-III 、 silica gel 、 EtOAc-hexanes 、 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 作用下， 以 氯仿 、 乙酸乙酯 为溶剂， 反应 16.0h， 以to give 5.4 g (88%) of 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 (compound 9) as an amorphous solid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：

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

  公开号：US20030199460A1

  公开（公告）日：2003-10-23

  Aminoalkyl glucosaminide phosphate (AGP) 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 glucosaminide ring and comprise three 3-alkanoyloxyalkanoyl residues. The compounds augment antibody production in immunized animals as well as stimulate cytokine production and activate macrophages. Compositions and 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酯（AGP）化合物，这些化合物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）基团在糖苷键中连接的结构。这些化合物在葡萄糖氨基糖环的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，同时也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作为辅助剂和免疫效应物质使用的组合物和方法。
• Processes for the production of aminoalkyl glucosaminide phosphate and disaccharide immunoeffectors, and intermediates therefor
  申请人：Johnson A. David

  公开号：US20050107600A1

  公开（公告）日：2005-05-19

  This invention relates to processes for production of alkylamino glucosaminide phosphate compounds, and of disaccharide compounds, including various novel intermediates and intermediate processes. In one aspect, glycosyl halides are produced by reaction of an O-silyl glycoside with a dihalomethyl alkyl ether.

  这项发明涉及生产烷基氨基葡糖氨磷酸化合物和二糖化合物的过程，包括各种新颖中间体和中间过程。在一个方面，通过将O-硅糖苷与二卤甲基烷醚反应来生产糖基卤化物。
• Processes for the production of aminoalkyl glucosaminide phosphate and disaccharide immunoeffectors and intermediates therefor
  申请人：——

  公开号：US20040267007A1

  公开（公告）日：2004-12-30

  This invention relates to processes for production of alkylamino glucosaminide phosphate compounds, and of disaccharide compounds, including various novel intermediates and intermediate processes. In one aspect, glycosyl halides are produced by reaction of an O-silyl glycoside with a dihalomethyl alkyl ether.

  本发明涉及生产烷基氨基葡萄糖胺磷酸化合物和二糖化合物的过程，包括各种新的中间体和中间体过程。在一个方面，通过将O-硅基糖苷与二卤甲基烷醚反应来生产糖基卤化物。
• PROCESSES FOR THE PRODUCTION OF AMINOALKYL GLUCOSAMINIDE PHOSPHATE AND DISACCHARIDE IMMUNOEFFECTORS, AND INTERMEDIATES THEREFOR
  申请人：Johnson A. David

  公开号：US20080033155A1

  公开（公告）日：2008-02-07

  This invention relates to processes for production of alkylamino glucosaminide phosphate compounds, and of disaccharide compounds, including various novel intermediates and intermediate processes. In one aspect, glycosyl halides are produced by reaction of an O-silyl glycoside with a dihalomethyl alkyl ether.

  本发明涉及生产烷基氨基葡糖氨磷酸化合物和二糖化合物的过程，包括各种新的中间体和中间过程。在一个方面，通过将O-硅糖苷与二卤甲基烷醚反应来产生糖基卤化物。