Tetradecanoic acid (S)-1-tetradecanoyloxymethyl-2-{(2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-[(2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-(benzyloxy-diisopropylamino-phosphanyloxymethyl)-tetrahydro-pyran-2-yloxymethyl]-tetrahydro-pyran-2-yloxy}-ethyl ester | 544687-04-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: Tetradecanoic acid (S)-1-tetradecanoyloxymethyl-2-{(2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-[(2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-(benzyloxy-diisopropylamino-phosphanyloxymethyl)-tetrahydro-pyran-2-yloxymethyl]-tetrahydro-pyran-2-yloxy}-ethyl ester
• 英文别名: [(2S)-3-[(2R,3R,4S,5R,6R)-6-[[(2R,3R,4S,5R,6R)-6-[[[di(propan-2-yl)amino]-phenylmethoxyphosphanyl]oxymethyl]-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxymethyl]-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxy-2-tetradecanoyloxypropyl] tetradecanoate
• CAS: 544687-04-9
• 化学式: C₉₈H₁₃₆NO₁₆P
• 分子量: 1615.13
• InChiKey: RUHSHBHMBKRVKS-OGPPTLFSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  23.6
• 重原子数：
  116
• 可旋转键数：
  62
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  167
• 氢给体数：
  0
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  、 Tetradecanoic acid (S)-1-tetradecanoyloxymethyl-2-{(2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-[(2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-(benzyloxy-diisopropylamino-phosphanyloxymethyl)-tetrahydro-pyran-2-yloxymethyl]-tetrahydro-pyran-2-yloxy}-ethyl ester 在 四氮唑 、 叔丁基过氧化氢 、 ammonium cerium(IV) nitrate 作用下， 以 二氯甲烷 、 水 、 甲苯 、 乙腈 为溶剂， 反应 1.75h， 生成
  参考文献：
  名称：

  Synthesis of Staphylococcus aureus lipoteichoic acid derivatives for determining the minimal structural requirements for cytokine induction

  摘要：

  For the investigation of the minimal structural requirements for cytokine induction, Staphylococcus aureus lipoteichoic acid derivatives with two, three, four, and five glycerophosphate backbone moieties, carrying each a D-alanyl residue, were needed. Based on two different glycerophosphate building blocks and 6b-O-phosphitylated gentiobiosyl diacylglycerol the desired target molecules (compounds 1-4) could be readily obtained and provided for biological studies. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.10.003
• 作为产物：
  描述：

  苄基N,N,N',N'-四异丙基亚磷酰二胺 、 1,2-di-O-myristoyl-3-O-[6-O-(2,3,4-tri-O-benzyl-β-D-glucopyranosyl)-2,3,4-tri-O-benzyl-β-D-glucopyranosyl]-sn-glycerol 以 二氯甲烷 为溶剂， 以79%的产率得到Tetradecanoic acid (S)-1-tetradecanoyloxymethyl-2-{(2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-[(2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-(benzyloxy-diisopropylamino-phosphanyloxymethyl)-tetrahydro-pyran-2-yloxymethyl]-tetrahydro-pyran-2-yloxy}-ethyl ester
  参考文献：
  名称：

  合成第一个完全活性的脂磷壁酸。

  摘要：

  DOI：

  10.1002/anie.200390243

文献信息

• A Staphylococcus aureus lipoteichoic acid (LTA) derived structural variant with two diacylglycerol residues
  作者：A STADELMAIER、I FIGUEROAPEREZ、S DEININGER、S VONAULOCK、T HARTUNG、R SCHMIDT

  DOI：10.1016/j.bmc.2006.05.055

  日期：2006.9.15

  Based on 1,2-O-isopropylidene-sn-glycerol five chiral building blocks containing differently modified glycerol residues were required for the synthesis of the target molecule 2. One of these building blocks is diacylglyceryl beta-gentiobioside carrying a phosphite residue at 6b-O position. Ligation of these five building blocks led to the desired glycerol phosphate backbone to which D-alanyl residues were attached, thus generating after O-deprotection the target molecule 2, a bisamphiphilic structural variant of Staphylococcus aureus LTA. This compound displayed higher potency in terms of cytokine release by human blood leukocytes than the monoamphiphilic variant LTA. (c) 2006 Elsevier Ltd. All rights reserved.