1-O-benzyl-2-O-methyl-3-O-octadecyl-rac-glycerol | 90940-90-2

• 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: 1-O-benzyl-2-O-methyl-3-O-octadecyl-rac-glycerol
• 英文别名: Benzene, [[2-methoxy-3-(octadecyloxy)propoxy]methyl]-；(2-methoxy-3-octadecoxypropoxy)methylbenzene
• CAS: 90940-90-2
• 化学式: C₂₉H₅₂O₃
• 分子量: 448.73
• InChiKey: RRIJQHDAINYAFG-UHFFFAOYSA-N

物化性质

• 沸点：
  525.4±40.0 °C(Predicted)
• 密度：
  0.918±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.2
• 重原子数：
  32
• 可旋转键数：
  24
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-O-benzyl-2-O-methyl-3-O-octadecyl-rac-glycerol 在 platinum(IV) oxide 、 palladium on activated charcoal 、 1,3-丙二醇 氢气 、 溶剂黄146 作用下， 以 甲苯 为溶剂， 反应 48.0h， 生成 rac-1-O-octadecyl-2-O-methylglycerol 3-phosphate
  参考文献：
  名称：

  Nucleoside conjugates. 7. Synthesis and antitumor activity of 1-.beta.-D-arabinofuranosylcytosine conjugates of ether lipids

  摘要：

  Three new 1-beta-D-arabinofuranosylcytosine conjugates of ether lipids (alkyl glycerols) linked by a pyrophosphate diester bond have been prepared and evaluated against mouse leukemia L1210 and P388. These include ara-CDP-rac-1-O-hexadecyl-2-O-palmitoylglycerol (9a) (ara-CDP = 1-beta-D-arabinofuranosylcytosine 5'-diphosphate), ara-CDP-rac-1-O-octadecyl-2-O-palmitoylglycerol (9b), and ara-CDP-rac-1-O-octadecyl-2-O-methylglycerol (9c). Among them, conjugate 9a produced significant increase in life span (200-293%) in mice bearing ip and ic implanted L1210 lymphoic leukemia at a total dose of 400-500 mg (406-508 mumol/kg). Significant schedule dependence was not observed when the conjugate was given ip once daily on day 1, days 1, 5, and 9, and days 1-5. The new conjugates are water soluble by sonication.

  DOI：

  10.1021/jm00160a041
• 作为产物：
  描述：

  硬脂基溴 在 sodium amide 作用下， 以 甲苯 为溶剂， 生成 1-O-benzyl-2-O-methyl-3-O-octadecyl-rac-glycerol
  参考文献：
  名称：

  Nucleoside conjugates. 7. Synthesis and antitumor activity of 1-.beta.-D-arabinofuranosylcytosine conjugates of ether lipids

  摘要：

  Three new 1-beta-D-arabinofuranosylcytosine conjugates of ether lipids (alkyl glycerols) linked by a pyrophosphate diester bond have been prepared and evaluated against mouse leukemia L1210 and P388. These include ara-CDP-rac-1-O-hexadecyl-2-O-palmitoylglycerol (9a) (ara-CDP = 1-beta-D-arabinofuranosylcytosine 5'-diphosphate), ara-CDP-rac-1-O-octadecyl-2-O-palmitoylglycerol (9b), and ara-CDP-rac-1-O-octadecyl-2-O-methylglycerol (9c). Among them, conjugate 9a produced significant increase in life span (200-293%) in mice bearing ip and ic implanted L1210 lymphoic leukemia at a total dose of 400-500 mg (406-508 mumol/kg). Significant schedule dependence was not observed when the conjugate was given ip once daily on day 1, days 1, 5, and 9, and days 1-5. The new conjugates are water soluble by sonication.

  DOI：

  10.1021/jm00160a041

文献信息

• Verfahren zur Herstellung von Glyzerinethern und ihre Verwendung
  申请人：BEHRINGWERKE Aktiengesellschaft

  公开号：EP0103273A1

  公开（公告）日：1984-03-21

  Es wird ein Verfahren zur Herstellung einer R- oder S-stereoisomeren oder racemischen Verbindung der allgemeinen Formel beschrieben, worin R1 eine Benzylgruppe ist, R2 und R3 verschieden sind und ein Wasserstoffatom oder eine C1-22-Alkylgruppe bedeuten, dadurch gekennzeichnet, daß man eine 1,2- oder 1,3-O-Benzyliden-Verbindung der allgemeinen Formel , worin R1 und R2 oder R1 und R3 zusammen eine Benzylidengruppe sind und jeweils R3 oder R2 eine C1-22-Alkylgruppe ist, in Gegenwart einer Lewissäure zu einer R- oder S-stereoisomeren oder racemischen Benzylether-Verbindung der allgemeinen Formell reduziert, worin R1 eine Benzylgruppe ist, R2 und R3 verschieden sind und ein Wasserstoffatom oder eine C1-22-Alkylgruppe bedeuten, und wobei bei einer racemischen Verbindung R1 und R3 untereinander austauschbar sind. Die auf diese Weise hergestellte Verbindung kann zur Herstellung einer R- oder S-stereoisomeren oder racemischen Verbindung der Formel II verwendet werden, worin entweder R2 oder R3 eine C1-22-Alkylgruppe ist und C1-22-Alkyl-, C1-22-Alkyl-, C1-16-Alkanoyl- oder Methansulfonylgruppe bedeuten.

  一种通式为 R-或 S-立体异构体或外消旋体的化合物的制备工艺 其中 R1 是苄基，R2 和 R3 不同，是氢原子或 C1-22 烷基，其特征在于通式的 1，2- 或 1，3-O-亚苄基化合物 其中 R1 和 R2 或 R1 和 R3 合在一起是亚苄基，每个 R3 或 R2 是 C1-22 烷基、在路易斯酸存在下还原成通式的 R-或 S-异构体或外消旋苄基醚化合物，其中 R1 是苄基，R2 和 R3 不同，分别是氢原子或 C1-22 烷基，在外消旋化合物中 R1 和 R3 可互换。 用这种方法制备的化合物可用于制备式 II 的 R-或 S-立体异构体或外消旋化合物 其中 R2 或 R3 是 C1-22 烷基，并且是 C1-22 烷基、C1-22 烷基、C1-16 烷酰基或甲磺酰基。
• Synthesis of alkyl glycerophospholipids through 1-o-benzyl-2-o-methyl-rac-glycerol
  作者：A. N. Pinchuk、B. I. Mitsner、V. I. Shvets

  DOI：10.1007/bf00766461

  日期：1992.2
• Synthesis of Alkyl Chain-Modified Ether Lipids and Evaluation of Their in Vitro Cytotoxicity
  作者：Empar Fos、Nuria Suesa、Liset Borras、Cinta Lobato、Patrizia Banfi、Romolo A. Gambetta、Franco Zunino、David Mauleon、Germano Carganico

  DOI：10.1021/jm00007a018

  日期：1995.3

  A series of alkyl lysophospholipid (ALP) analogs of ET-18-OCH3 (1-O-octadecyl-2-O-methylrac-glycero-3-phosphocholine) containing modifications in the long C-1 chain has been synthesized and evaluated in human tumor cell line cytotoxicity assays. The compounds have also been evaluated in platelet activating factor (PAF) receptor agonism and hemolysis tests. Two modifications have been studied, introduction of a carbonyl group at different positions of the C-1 chain and branching of this chain, in some compounds with incorporation of a phenyl group. Several compounds showed a cytotoxic potency comparable to that of the reference compound ET-18-OCH3, associated with reduced proaggregating and hemolytic effects. The two enantiomers of 1-0-(7-oxooctadecyl)-2-O-methyl-rac-glycero-3-phospho choline (2) showed the same level of cytotoxicity or antiproliferative activity, with the PAF-agonistic effect confined to R-2. The very low stereoselectivity found in the in vitro cytotoxicity confirms earlier results and indicates a lack of stereospecific interactions with a macromolecular target.
• Nucleoside conjugates. 7. Synthesis and antitumor activity of 1-.beta.-D-arabinofuranosylcytosine conjugates of ether lipids
  作者：Chung Il Hong、Seung Ho An、David J. Buchheit、Alexander Nechaev、Alan J. Kirisits、Charles R. West、Wolfgang E. Berdel

  DOI：10.1021/jm00160a041

  日期：1986.10

  Three new 1-beta-D-arabinofuranosylcytosine conjugates of ether lipids (alkyl glycerols) linked by a pyrophosphate diester bond have been prepared and evaluated against mouse leukemia L1210 and P388. These include ara-CDP-rac-1-O-hexadecyl-2-O-palmitoylglycerol (9a) (ara-CDP = 1-beta-D-arabinofuranosylcytosine 5'-diphosphate), ara-CDP-rac-1-O-octadecyl-2-O-palmitoylglycerol (9b), and ara-CDP-rac-1-O-octadecyl-2-O-methylglycerol (9c). Among them, conjugate 9a produced significant increase in life span (200-293%) in mice bearing ip and ic implanted L1210 lymphoic leukemia at a total dose of 400-500 mg (406-508 mumol/kg). Significant schedule dependence was not observed when the conjugate was given ip once daily on day 1, days 1, 5, and 9, and days 1-5. The new conjugates are water soluble by sonication.