[(2R,3S,4R,5R,6S)-3-hydroxy-2-(phenylmethoxymethyl)-6-prop-2-enoxy-5-(2,2,2-trichloroethoxycarbonylamino)oxan-4-yl] (3R)-3-dodecoxytetradecanoate | 339317-29-2

• 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: [(2R,3S,4R,5R,6S)-3-hydroxy-2-(phenylmethoxymethyl)-6-prop-2-enoxy-5-(2,2,2-trichloroethoxycarbonylamino)oxan-4-yl] (3R)-3-dodecoxytetradecanoate
• CAS: 339317-29-2
• 化学式: C₄₅H₇₄Cl₃NO₉
• 分子量: 879.443
• InChiKey: GHFYSTANPLRGQK-JVXWVHAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.9
• 重原子数：
  58
• 可旋转键数：
  36
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  122
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [(2R,3S,4R,5R,6S)-3-hydroxy-2-(phenylmethoxymethyl)-6-prop-2-enoxy-5-(2,2,2-trichloroethoxycarbonylamino)oxan-4-yl] (3R)-3-dodecoxytetradecanoate 在 四氮唑 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 生成 [(2R,3S,4R,5R,6S)-3-bis(phenylmethoxy)phosphoryloxy-2-(phenylmethoxymethyl)-6-prop-2-enoxy-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 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 、 锌 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 、 乙腈 为溶剂， 生成 [(2R,3S,4R,5R,6S)-3-hydroxy-2-(phenylmethoxymethyl)-6-prop-2-enoxy-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

文献信息

• SYNTHETIC LIPID-A ANALOGS AND USES THEREOF
  申请人：Oncothyreon Inc.

  公开号：EP1232168B1

  公开（公告）日：2011-08-03
• 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.