[(2S,3R,4R,5S,6R)-5-bis(phenylmethoxy)phosphoryloxy-2-hydroxy-6-(phenylmethoxymethyl)-3-(2,2,2-trichloroethoxycarbonylamino)oxan-4-yl] (3R)-3-dodecoxytetradecanoate | 474670-20-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2S,3R,4R,5S,6R)-5-bis(phenylmethoxy)phosphoryloxy-2-hydroxy-6-(phenylmethoxymethyl)-3-(2,2,2-trichloroethoxycarbonylamino)oxan-4-yl] (3R)-3-dodecoxytetradecanoate
• CAS: 474670-20-7
• 化学式: C₅₆H₈₃Cl₃NO₁₂P
• 分子量: 1099.61
• InChiKey: WCOMHHQTXLTUHM-PBKPEZRASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.7
• 重原子数：
  73
• 可旋转键数：
  41
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  157
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  三氯乙腈 、 [(2S,3R,4R,5S,6R)-5-bis(phenylmethoxy)phosphoryloxy-2-hydroxy-6-(phenylmethoxymethyl)-3-(2,2,2-trichloroethoxycarbonylamino)oxan-4-yl] (3R)-3-dodecoxytetradecanoate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 以61%的产率得到[(2R,3S,4R,5R,6R)-3-bis(phenylmethoxy)phosphoryloxy-2-(phenylmethoxymethyl)-6-(2,2,2-trichloroethanimidoyl)oxy-5-(2,2,2-trichloroethoxycarbonylamino)oxan-4-yl] (3R)-3-dodecoxytetradecanoate
  参考文献：
  名称：

  Lipid A structures containing novel lipid moieties: synthesis and adjuvant properties

  摘要：

  Structurally well-defined immune stimulatory molecules are important components of new generation molecular vaccines. In this paper, the design and synthesis of two lipid A analogues containing an unnatural tri-lipid acyl group are described. In a totally synthetic liposomal vaccine system, these re-designed lipid A analogues demonstrate potent immune stimulatory properties including antigen specific T-cell activation. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00362-1
• 作为产物：
  描述：

  (3R)-3-hydroxytetradecanoic acid phenacyl ester 在 四氮唑 、 4-二甲氨基吡啶 、 二甲胺基甲硼烷 、 三氟化硼乙醚 、 potassium carbonate 、 溶剂黄146 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 间氯过氧苯甲酸 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 、 1,2-二氯乙烷 、 乙腈 为溶剂， 生成 [(2S,3R,4R,5S,6R)-5-bis(phenylmethoxy)phosphoryloxy-2-hydroxy-6-(phenylmethoxymethyl)-3-(2,2,2-trichloroethoxycarbonylamino)oxan-4-yl] (3R)-3-dodecoxytetradecanoate
  参考文献：
  名称：

  Lipid A structures containing novel lipid moieties: synthesis and adjuvant properties

  摘要：

  Structurally well-defined immune stimulatory molecules are important components of new generation molecular vaccines. In this paper, the design and synthesis of two lipid A analogues containing an unnatural tri-lipid acyl group are described. In a totally synthetic liposomal vaccine system, these re-designed lipid A analogues demonstrate potent immune stimulatory properties including antigen specific T-cell activation. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00362-1

文献信息

• Lipid A structures containing novel lipid moieties: synthesis and adjuvant properties
  作者：Zi-Hua Jiang、Mimi V Bach、Wladyslaw A Budzynski、Mark J Krantz、R.Rao Koganty、B.Michael Longenecker

  DOI：10.1016/s0960-894x(02)00362-1

  日期：2002.8

  Structurally well-defined immune stimulatory molecules are important components of new generation molecular vaccines. In this paper, the design and synthesis of two lipid A analogues containing an unnatural tri-lipid acyl group are described. In a totally synthetic liposomal vaccine system, these re-designed lipid A analogues demonstrate potent immune stimulatory properties including antigen specific T-cell activation. (C) 2002 Elsevier Science Ltd. All rights reserved.