(R)-3-((tert-butyldimethylsilyl)oxy)-2-hydroxypropyl palmitate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (R)-3-((tert-butyldimethylsilyl)oxy)-2-hydroxypropyl palmitate
• 英文别名: [(2R)-3-[tert-butyl(dimethyl)silyl]oxy-2-hydroxypropyl] hexadecanoate
• 化学式: C₂₅H₅₂O₄Si
• 分子量: 444.771
• InChiKey: VHVIBFYZISBVCW-HSZRJFAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.39
• 重原子数：
  30
• 可旋转键数：
  21
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-3-((tert-butyldimethylsilyl)oxy)-2-hydroxypropyl palmitate 在 4-二甲氨基吡啶 、 boron trifluoride acetonitrile 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 正庚烷 、 二氯甲烷 为溶剂， 反应 18.17h， 生成 1,2-二棕榈酰-sn-丙三醇
  参考文献：
  名称：

  Total Synthesis of an Immunogenic Trehalose Phospholipid from Salmonella Typhi and Elucidation of Its sn-Regiochemistry by Mass Spectrometry

  摘要：

  Diphosphatidyltrehalose (diPT) is an immunogenic glycolipid, recently isolated from Salmonella Typhi. Despite rigorous structure elucidation, the sn-position of the acyl chains on the glycerol backbone had not been unequivocally established. A stereoselective synthesis of diPT and its regioisomer is reported herein. Using a hybrid MS3 approach combining collisional dissociation and ultraviolet photodissociation mass spectrometry for analysis of the regioisomers and natural diPT, the regiochemistry of the acyl chains of this abundant immunostimulatory glycolipid was established.

  DOI：

  10.1021/acs.orglett.9b01725
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 在 咪唑 、 (S,S)-(+)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminocobalt(II) 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 23.33h， 生成 (R)-3-((tert-butyldimethylsilyl)oxy)-2-hydroxypropyl palmitate
  参考文献：
  名称：

  Total Synthesis of an Immunogenic Trehalose Phospholipid from Salmonella Typhi and Elucidation of Its sn-Regiochemistry by Mass Spectrometry

  摘要：

  Diphosphatidyltrehalose (diPT) is an immunogenic glycolipid, recently isolated from Salmonella Typhi. Despite rigorous structure elucidation, the sn-position of the acyl chains on the glycerol backbone had not been unequivocally established. A stereoselective synthesis of diPT and its regioisomer is reported herein. Using a hybrid MS3 approach combining collisional dissociation and ultraviolet photodissociation mass spectrometry for analysis of the regioisomers and natural diPT, the regiochemistry of the acyl chains of this abundant immunostimulatory glycolipid was established.

  DOI：

  10.1021/acs.orglett.9b01725