Octadecanoic acid 3-((2R,3R,4S,5S,6S)-6-acetylsulfanylmethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-2-hydroxy-propyl ester | 760178-15-2

• 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: Octadecanoic acid 3-((2R,3R,4S,5S,6S)-6-acetylsulfanylmethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-2-hydroxy-propyl ester
• CAS: 760178-15-2
• 化学式: C₅₀H₇₂O₉S
• 分子量: 849.182
• InChiKey: HJAHMUCJKQGLOJ-UMVMTKJNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.93
• 重原子数：
  60.0
• 可旋转键数：
  32.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  109.75
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  Octadecanoic acid 3-((2R,3R,4S,5S,6S)-6-acetylsulfanylmethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-2-hydroxy-propyl ester 在 Oxone 、 potassium acetate 、 溶剂黄146 作用下， 以85.9%的产率得到Sodium; [(2S,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-(2-hydroxy-3-octadecanoyloxy-propoxy)-tetrahydro-pyran-2-yl]-methanesulfonate
  参考文献：
  名称：

  Synthesis of an immunosuppressant SQAG9 and determination of the binding peptide by T7 phage display

  摘要：

  SQAG9, a new class of immunosuppressive sulfoquinovosylacylglycerol, and its biotinylated derivatives have been synthesized. A T7 Phage library, composed of random cDNA fragments from Drosophila melanogaster, displayed a possible binding peptide of 14 amino acids. The immobilized synthetic peptide on a sensor chip showed a dissociation constant of K-D = 1.5 x 10(-6) against SQAG9 in a surface plasmon resonance experiment. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.05.085
• 作为产物：
  描述：

  allyl 2,3,4-tri-O-benzyl-β-D-glucopyranoside 在 吡啶 、 4-二甲氨基吡啶 、 四氧化锇 、 N-甲基吲哚酮 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 、 叔丁醇 为溶剂， 生成 Octadecanoic acid 3-((2R,3R,4S,5S,6S)-6-acetylsulfanylmethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-2-hydroxy-propyl ester
  参考文献：
  名称：

  Synthesis of an immunosuppressant SQAG9 and determination of the binding peptide by T7 phage display

  摘要：

  SQAG9, a new class of immunosuppressive sulfoquinovosylacylglycerol, and its biotinylated derivatives have been synthesized. A T7 Phage library, composed of random cDNA fragments from Drosophila melanogaster, displayed a possible binding peptide of 14 amino acids. The immobilized synthetic peptide on a sensor chip showed a dissociation constant of K-D = 1.5 x 10(-6) against SQAG9 in a surface plasmon resonance experiment. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.05.085