4-[(R)-3-tetradecanoyloxytetradecanoylamino]butyl 2-deoxy-4-O-diphenylphosphono-3-O-[(R)-3-tetradecanoyoxytetradecanoyl]-2-[(R)-3-tetradecanoyloxytetradecanoylamino]-β-D-glucopyranoside | 216014-67-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-[(R)-3-tetradecanoyloxytetradecanoylamino]butyl 2-deoxy-4-O-diphenylphosphono-3-O-[(R)-3-tetradecanoyoxytetradecanoyl]-2-[(R)-3-tetradecanoyloxytetradecanoylamino]-β-D-glucopyranoside
• 英文别名: [(2R,3S,4R,5R,6R)-3-diphenoxyphosphoryloxy-2-(hydroxymethyl)-5-[[(3R)-3-tetradecanoyloxytetradecanoyl]amino]-6-[4-[[(3R)-3-tetradecanoyloxytetradecanoyl]amino]butoxy]oxan-4-yl] (3R)-3-tetradecanoyloxytetradecanoate
• CAS: 216014-67-4
• 化学式: C₁₀₆H₁₈₇N₂O₁₇P
• 分子量: 1792.63
• InChiKey: SWZSDSDPNKFOST-HTZMHQMZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  36.8
• 重原子数：
  126
• 可旋转键数：
  94
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  247
• 氢给体数：
  3
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  4-[(R)-3-tetradecanoyloxytetradecanoylamino]butyl 2-deoxy-4-O-diphenylphosphono-3-O-[(R)-3-tetradecanoyoxytetradecanoyl]-2-[(R)-3-tetradecanoyloxytetradecanoylamino]-β-D-glucopyranoside 在 platinum(IV) oxide 氢气 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 生成 (R)-3-Tetradecanoyloxy-tetradecanoic acid (2R,3S,4R,5R,6R)-2-hydroxymethyl-3-phosphonooxy-5-((R)-3-tetradecanoyloxy-tetradecanoylamino)-6-[4-((R)-3-tetradecanoyloxy-tetradecanoylamino)-butoxy]-tetrahydro-pyran-4-yl ester
  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 、 4-[(R)-3-tetradecanoyloxytetradecanoylamino]butyl 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 在 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 、 锌 作用下， 以60%的产率得到4-[(R)-3-tetradecanoyloxytetradecanoylamino]butyl 2-deoxy-4-O-diphenylphosphono-3-O-[(R)-3-tetradecanoyoxytetradecanoyl]-2-[(R)-3-tetradecanoyloxytetradecanoylamino]-β-D-glucopyranoside
  参考文献：
  名称：

  Aminoalkyl glucosamine phosphate compounds and their use as adjuvants and immunoeffectors

  摘要：

  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。

  公开号：

  US06355257B1