(S)-2,3-dihydroxypropyl 2-bromoacetate | 925670-99-1

• 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: (S)-2,3-dihydroxypropyl 2-bromoacetate
• 英文别名: (s)-2,3-Dihydroxypropyl 2-bromoacetate；[(2S)-2,3-dihydroxypropyl] 2-bromoacetate
• CAS: 925670-99-1
• 化学式: C₅H₉BrO₄
• 分子量: 213.028
• InChiKey: OBIZXLAEEKEFMZ-BYPYZUCNSA-N

物化性质

• 沸点：
  326.8±27.0 °C(Predicted)
• 密度：
  1.730±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-2,3-dihydroxypropyl 2-bromoacetate 、 棕榈酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以73%的产率得到3-O-bromoacetyl-1,2-di-O-palmitoyl-sn-glycerol
  参考文献：
  名称：

  Synthesis of Boron Cluster Lipids:  closo-Dodecaborate as an Alternative Hydrophilic Function of Boronated Liposomes for Neutron Capture Therapy

  摘要：

  [GRAPHIC]We succeeded in the synthesis of the double-tailed boron cluster lipids 4a-c and 5a-c, which have a B12H11S moiety as a hydrophilic function, by S-alkylation of B12H11SH (BSH) with bromoacetyl and chloroacetocarbamate derivatives of diacylglycerols for a liposomal boron delivery system on neutron capture therapy. Calcein encapsulation experiments revealed that the liposomes, prepared from the boron cluster lipid 4b, DMPC, PEG-DSPE, and cholesterol, are stable at 37 degrees C in FBS solution for 24 h.

  DOI：

  10.1021/ol062840+
• 作为产物：
  描述：

  ((S)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl 2-bromoacetate 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以38%的产率得到(S)-2,3-dihydroxypropyl 2-bromoacetate
  参考文献：
  名称：

  Synthesis of Boron Cluster Lipids:  closo-Dodecaborate as an Alternative Hydrophilic Function of Boronated Liposomes for Neutron Capture Therapy

  摘要：

  [GRAPHIC]We succeeded in the synthesis of the double-tailed boron cluster lipids 4a-c and 5a-c, which have a B12H11S moiety as a hydrophilic function, by S-alkylation of B12H11SH (BSH) with bromoacetyl and chloroacetocarbamate derivatives of diacylglycerols for a liposomal boron delivery system on neutron capture therapy. Calcein encapsulation experiments revealed that the liposomes, prepared from the boron cluster lipid 4b, DMPC, PEG-DSPE, and cholesterol, are stable at 37 degrees C in FBS solution for 24 h.

  DOI：

  10.1021/ol062840+