(R)-(+)-1-stearoyl-3-(tert-butyldimethylsilyl)-sn-glycerol | 110193-08-3

• 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)-(+)-1-stearoyl-3-(tert-butyldimethylsilyl)-sn-glycerol
• 英文别名: (R)-3-[(tert-butyldimethylsilyl)oxy]-2-hydroxypropyl stearate；(R)-1-octadecanoyl-3-O-tert-butyldimethylsilyl-glycerol；[(2R)-3-[tert-butyl(dimethyl)silyl]oxy-2-hydroxypropyl] octadecanoate
• CAS: 110193-08-3
• 化学式: C₂₇H₅₆O₄Si
• 分子量: 472.825
• InChiKey: QBXQHZJULOWZAP-RUZDIDTESA-N

物化性质

• 沸点：
  521.8±40.0 °C(Predicted)
• 密度：
  0.913±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.17
• 重原子数：
  32
• 可旋转键数：
  23
• 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)-(+)-1-stearoyl-3-(tert-butyldimethylsilyl)-sn-glycerol 在 吡啶 、 N-溴代丁二酰亚胺(NBS) 、 水 、 二甲基亚砜 作用下， 以 四氢呋喃 为溶剂， 生成 (2S)-3-羟基-1,2-丙烷二基二硬脂酸酯
  参考文献：
  名称：

  A new, asymmetric synthesis of lipids and phospholipids

  摘要：

  DOI：

  10.1021/jo00231a025
• 作为产物：
  描述：

  硬脂酸 在 盐酸 、 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 33.58h， 生成 (R)-(+)-1-stearoyl-3-(tert-butyldimethylsilyl)-sn-glycerol
  参考文献：
  名称：

  含光反应和可点击官能团的糖基磷脂酰肌醇锚双功能化核心结构的设计与合成

  摘要：

  糖基磷脂酰肌醇 (GPI) 锚的核心结构的双功能衍生物具有可点击的炔基和光反应性二氮丙啶基团，分别连接到 GPI 葡糖胺和脂质部分，由肌醇、d-葡糖胺和 ( R )-合成1,2- O-丙酮化甘油。目标分子应该有助于研究细胞膜中的 GPI 相互作用成分，这些成分在 GPI 锚定蛋白的信号转导和其他生物学功能中起着关键作用。

  DOI：

  10.1021/acs.joc.2c00901

文献信息

• Catalytic synthesis of enantiopure mixed diacylglycerols – synthesis of a major M. tuberculosis phospholipid and platelet activating factor
  作者：Peter Fodran、Adriaan J. Minnaard

  DOI：10.1039/c3ob41483c

  日期：——

  An efficient catalytic one-pot synthesis of TBDMS-protected diacylglycerols has been developed, starting from enantiopure glycidol. Subsequent migration-free deprotection leads to stereo- and regiochemically pure diacylglycerols. This novel strategy has been applied to the synthesis of a major Mycobacterium tuberculosis phospholipid, its desmethyl analogue, and platelet activating factor.

  一种高效催化的一锅法合成TBDMS保护的二酰基甘油已被开发出来，从手性纯甘油酸环丙烷开始，随后无迁移的脱保护步骤产生立体化学和区域化学纯的二酰基甘油。这种新颖的策略已应用于合成主要的结核分枝杆菌磷脂、其脱甲基类似物和血小板活化因子。
• Prostaglandin phospholipid conjugates with unusual biophysical and cytotoxic properties
  作者：Palle J. Pedersen、Sidsel K. Adolph、Thomas L. Andresen、Mogens W. Madsen、Robert Madsen、Mads H. Clausen

  DOI：10.1016/j.bmcl.2010.06.054

  日期：2010.8

  The synthesis of two secretory phospholipase A(2) IIA sensitive 15-deoxy-Delta(12,14)-prostaglandin J(2) phospholipid conjugates is described and their biophysical and biological properties are reported. The conjugates spontaneously form particles in the liposome size region upon dispersion in an aqueous buffer and both phospholipids are hydrolyzed by phospholipase A(2), but with different conversion rates and extent of hydrolysis. The cytotoxicity was evaluated in HT-29 and Colo205 cells and the conjugates induced cell death in the presence of phospholipase A(2) and surprisingly also in the absence of the enzyme. (C) 2010 Elsevier Ltd. All rights reserved.
• Liposomal Formulation of Retinoids Designed for Enzyme Triggered Release
  作者：Palle J. Pedersen、Sidsel K. Adolph、Arun K. Subramanian、Ahmad Arouri、Thomas L. Andresen、Ole G. Mouritsen、Robert Madsen、Mogens W. Madsen、Günther H. Peters、Mads H. Clausen

  DOI：10.1021/jm100190c

  日期：2010.5.13

  The design of retinoid phospholipid prodrugs is described based on molecular dynamics simulations and cytotoxicity studies of synthetic retinoid esters. The prodrugs are degradable by secretory phospholipase A(2) IIA and have potential in liposomal drug delivery targeting tumors. We have synthesized four different retinoid phospholipid prodrugs and shown that they form particles in the liposome size region with average diameters of 94-118 nm. Upon subjection to phospholipase A(2), the lipid prodrugs were hydrolyzed, releasing cytotoxic retinoids and lysolipids. The formulated lipid prodrugs displayed IC50 values in the range of 3-19 mu M toward HT-29 and Colo205 colon cancer cells in the presence of phospholipase A(2), while no significant cell death was observed in the absence of the enzyme.
• BURGOS, CARMEN E.;AYER, DONALD E.;JOHNSON, ROY A., J. ORG. CHEM., 52,(1987) N 22, 4973-4977
  作者：BURGOS, CARMEN E.、AYER, DONALD E.、JOHNSON, ROY A.

  DOI：——

  日期：——
• A new, asymmetric synthesis of lipids and phospholipids
  作者：Carmen E. Burgos、Donald E. Ayer、Roy A. Johnson

  DOI：10.1021/jo00231a025

  日期：1987.10