(R)-2,3-di-(tert-butyldimethylsilyloxy)-1-propanol | 1159279-49-8

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (R)-2,3-di-(tert-butyldimethylsilyloxy)-1-propanol
• 英文别名: (R)-2,3-bis((tert-butyldimethylsilyl)oxy)propan-1-ol；(R)-1,2-di-O-tert-butyldimethylsilyl-glycerol；(2R)-2,3-bis[[tert-butyl(dimethyl)silyl]oxy]propan-1-ol
• CAS: 1159279-49-8
• 化学式: C₁₅H₃₆O₃Si₂
• 分子量: 320.62
• InChiKey: CJUQBPWNERKOFK-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.39
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-2,3-di-(tert-butyldimethylsilyloxy)-1-propanol 在 sodium chlorite 、 sodium dihydrogenphosphate 、 lithium aluminium tetrahydride 、 正丁基锂 、 2-甲基-2-丁烯 、 草酰氯 、 palladium 10% on activated carbon 、 氢气 、 sodium hydride 、 氟化氢吡啶 、 N,N-二异丙基乙胺 、 bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 二氯甲烷 、 水 、 二甲基亚砜 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 70.25h， 生成
  参考文献：
  名称：

  α-羟基羧酸部分侧链修饰的Destruxin E类似物的平行合成和生物学评估

  摘要：

  已经实现了在α-羟基羧酸部分具有各种功能基团的destruxin E类似物的合成和生物学评估。α-羟基羧酸侧链中的（S）-环氧部分可能是在较低浓度下诱导OCL形态变化的重要因素。

  DOI：

  10.1002/ejoc.201801826
• 作为产物：
  描述：

  (R)-1,2-di-(tert-butyldimethylsilyloxy)-3-(tetrahydropyran-2-yloxy)propane 在 氯化二乙基铝 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以92%的产率得到(R)-2,3-di-(tert-butyldimethylsilyloxy)-1-propanol
  参考文献：
  名称：

  α-羟基羧酸部分侧链修饰的Destruxin E类似物的平行合成和生物学评估

  摘要：

  已经实现了在α-羟基羧酸部分具有各种功能基团的destruxin E类似物的合成和生物学评估。α-羟基羧酸侧链中的（S）-环氧部分可能是在较低浓度下诱导OCL形态变化的重要因素。

  DOI：

  10.1002/ejoc.201801826

文献信息

• Stereospecific synthesis of phosphatidylglycerol using a cyanoethyl phosphoramidite precursor
  作者：Zachary J. Struzik、Ashley N. Weerts、Judith Storch、David H. Thompson

  DOI：10.1016/j.chemphyslip.2020.104933

  日期：2020.9

  Phosphatidylglycerols (PG) are a family of naturally occurring phospholipids that are responsible for critical operations within cells. PG are characterized by an (R) configuration in the diacyl glycerol backbone and an (S) configuration in the phosphoglycerol head group. Herein, we report a synthetic route to provide control over the PG stereocenters as well as control of the acyl chain identity.

  磷脂酰甘油 (PG) 是一类天然存在的磷脂，负责细胞内的关键操作。PG 的特征在于二酰基甘油骨架中的 ( R ) 构型和磷酸甘油头基中的 ( S ) 构型。在这里，我们报告了一种合成路线，以提供对 PG 立体中心的控制以及对酰基链身份的控制。
• Synthesis and Biophysical Characterization of Chlorambucil Anticancer Ether Lipid Prodrugs
  作者：Palle J. Pedersen、Mikkel S. Christensen、Tristan Ruysschaert、Lars Linderoth、Thomas L. Andresen、Fredrik Melander、Ole G. Mouritsen、Robert Madsen、Mads H. Clausen

  DOI：10.1021/jm900091h

  日期：2009.5.28

  The synthesis and biophysical characterization of four prodrug ether phospholipid conjugates are described. The lipids are prepared from the anticancer drug chlorambucil and have C16 and C18 ether chains with phosphatidylcholine or phosphatidylglycerol headgroups. All four prodrugs have the ability to form unilamellar liposomes (86-125 nm) and are hydrolyzed by phospholipase A(2), resulting in chlorambucil release. Liposomal formulations of prodrug lipids displayed cytotoxicity toward HT-29, MT-3, and ES-2 cancer cell lines in the presence of phospholipase A(2), with IC50 values in the 8-36 mu M range.
• F₂-Isoprostanes in HDL are bound to neutral lipids and phospholipids
  作者：Julie M. Proudfoot、Anne E. Barden、Kevin D. Croft、Jean-Marie Galano、Thierry Durand、Valérie Bultel-Poncé、Martin Giera、Trevor A. Mori

  DOI：10.1080/10715762.2016.1250262

  日期：2016.12.1

  Low HDL cholesterol (HDL-C) is a risk factor for coronary artery disease (CAD). However, interventions that raise HDL-C have failed to reduce cardiovascular events. We previously reported that HDL is the main carrier of plasma F-2-isoprostanes (F-2-IsoPs) that are markers of oxidative stress formed upon oxidation of arachidonic acid. F-2-IsoPs are predominantly associated with phospholipids. However, there is evidence that F-2-IsoPs in the liver of rats treated with carbon tetrachloride associate with the neutral lipids. To date it is not known whether F-2-IsoPs are found in the neutral lipids in HDL in humans. Possible candidate neutral lipids include cholesteryl esters, triglycerides, diglycerides, and monoglycerides. This study aimed to identify the lipid classes within native and oxidized HDL that contain F-2-IsoPs. We showed that F-2-IsoPs in HDL are bound to neutral lipids as well as phospholipids. HDL-3 contained the highest concentration of F-2-IsoPs in all lipid classes before and after in vitro oxidation. Using targeted LC/MS and high resolution MS, we were unable to provide conclusive evidence for the presence of the synthesized standards 15(R)-15-F-2t-isoP cholesterol and 1-ent-15(RS)-15-F-2t-isoprostanoyl-sn-glycerol in the neutral lipids of HDL. Our findings show that oxidized lipids such as F-2-IsoPs are found in the core and surface of HDL. However, the exact molecular species remain to be definitively characterized. Future studies are required to determine whether the presence of F-2-IsoPs in neutral lipids alters HDL function.
• Parallel Synthesis and Biological Evaluation of Destruxin E Analogs Modified with a Side Chain in the α-Hydroxycarboxylic Acid Moiety
  作者：Masahito Yoshida、Kenta Adachi、Hayato Murase、Hiroshi Nakagawa、Takayuki Doi

  DOI：10.1002/ejoc.201801826

  日期：2019.2.21

  Synthesis and biological evaluation of destruxin E analogs possessing various functional groups in the α‐hydroxycarboxylic acid moiety have been achieved. The (S)‐epoxide moiety in the side chain of α‐hydroxycarboxylic acid could be an essential factor for the induction of morphological changes in OCLs at a lower concentration.

  已经实现了在α-羟基羧酸部分具有各种功能基团的destruxin E类似物的合成和生物学评估。α-羟基羧酸侧链中的（S）-环氧部分可能是在较低浓度下诱导OCL形态变化的重要因素。