1-O-hexadecyl-2-O-methyl-3-O-(p-tolylsulfonyl)-sn-glycerol | 122822-32-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-O-hexadecyl-2-O-methyl-3-O-(p-tolylsulfonyl)-sn-glycerol
• 英文别名: [(2R)-3-hexadecoxy-2-methoxypropyl] 4-methylbenzenesulfonate
• CAS: 122822-32-6
• 化学式: C₂₇H₄₈O₅S
• 分子量: 484.741
• InChiKey: PFZXDZXKEJAZDT-AREMUKBSSA-N

物化性质

• 沸点：
  570.7±45.0 °C(Predicted)
• 密度：
  1.008±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.21
• 重原子数：
  33.0
• 可旋转键数：
  22.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1-O-hexadecyl-2-O-methyl-3-O-(p-tolylsulfonyl)-sn-glycerol 在 18-冠醚-6 potassium superoxide 作用下， 以 乙二醇二甲醚 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以81%的产率得到十六基甲基甘油
  参考文献：
  名称：

  Regiospecific opening of glycidyl derivatives mediated by boron trifluoride. Asymmetric synthesis of ether-linked phospholipids

  摘要：

  DOI：

  10.1021/jo00280a034
• 作为产物：
  描述：

  (R)-对甲苯磺酸缩水甘油酯 在 2,6-二叔丁基-4-甲基吡啶 、 三氟化硼乙醚 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 40.0h， 生成 1-O-hexadecyl-2-O-methyl-3-O-(p-tolylsulfonyl)-sn-glycerol
  参考文献：
  名称：

  Regiospecific opening of glycidyl derivatives mediated by boron trifluoride. Asymmetric synthesis of ether-linked phospholipids

  摘要：

  DOI：

  10.1021/jo00280a034

文献信息

• Synthesis and antineoplastic properties of ether-linked thioglycolipids
  作者：Pedro N. Guivisdalsky、Robert Bittman、Zigrida Smith、Merle L. Blank、Fred Snyder、Sandra Howard、Hassan Salari

  DOI：10.1021/jm00171a042

  日期：1990.9

  Ether-linked glycero-alpha- and beta-D-glucopyranosides and glycero-1-thio-alpha- and beta-D-glucopyranosides have been synthesized by modifications of the Königs-Knorr procedure, and their antitumor activities have been evaluated. The bioactivities of these compounds have been evaluated in five different cell lines (WEHI 3B, C653, X63/OMIL3, R6X-B15, and HL-60) and compared with the activities of 1-O-hexadecyl-2-O-methyl-sn-3-glycerophosphocholine (GPC) and its enantiomer, 3-O-hexadecyl-2-O-methyl-sn-1-GPC. The results indicate that a alpha-D-thioglucopyranoside [1-O-hexadecyl-2-O-methyl-3-S-(alpha-D-1'- thioglucopyranosyl-sn-glycerol)] is selective with respect to its action on target cells, with high activity for killing of WEHI 3B and C653 cells as determined by inhibition of [3H]thymidine incorporation into DNA and HL-60 cell cytotoxicity, but unable to induce aggregation of rabbit platelets at 10(-5) M. The corresponding beta-linked thioglycolipid was ineffective with respect to cytotoxicity against each cell line tested, indicating the importance of configuration at the anomeric position; the beta-thioglycoside was also ineffective with respect to inducing platelet aggregation. 1-O-Hexadecyl-2-O-methyl-sn-3-GPC and 3-O-hexadecyl-2-O-methyl-sn-1-GPC were potent inhibitors of growth of each cell line tested but also caused rabbit platelet aggregation at concentrations greater than or equal to 10(-7) M. Thus, 3-S-(alpha-thioglycopyranosyl)-sn- glycerols bearing a long-chain O-alkyl group at the sn-1 position and a methoxy group at the sn-2 position of glycerol appear to be a promising class of antineoplastic agents with lower risk of inducing thrombosis than the widely studied platelet activating factor analogue, 1-O-octadecyl-2-O-methyl-rac-3-GPC.
• GUIVISDALSKY, PEDRO N.;BITTMAN, ROBETR;SMITH, ZIGRIDA;BLANK, MERLE L.;SNY+, J. MED. CHEM., 33,(1990) N, C. 2614-2621
  作者：GUIVISDALSKY, PEDRO N.、BITTMAN, ROBETR、SMITH, ZIGRIDA、BLANK, MERLE L.、SNY+

  DOI：——

  日期：——