(S)-sn-1,2-二辛酰-3-苄基甘油 | 688021-88-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 中文名称: (S)-sn-1,2-二辛酰-3-苄基甘油
• 英文名称: 1,2-di-O-octanoyl-3-O-benzyl-sn-glycerol
• 英文别名: (S)-1-benzyloxy-2,3-bis-octanoyloxy-propane；(S)-1-Benzyloxy-2,3-bis-octanoyloxy-propan；(S)-sn-1,2-Dioctanoyl-3-benzylglycerol；[(2S)-2-octanoyloxy-3-phenylmethoxypropyl] octanoate
• CAS: 688021-88-7
• 化学式: C₂₆H₄₂O₅
• 分子量: 434.616
• InChiKey: YKYDQMIJNZBEQD-DEOSSOPVSA-N

物化性质

• 溶解度：
  可溶于二氯甲烷、乙醚、乙酸乙酯、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  31
• 可旋转键数：
  21
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-sn-1,2-二辛酰-3-苄基甘油 在 palladium on activated charcoal 四氮唑 、 氢气 、 溶剂黄146 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 二氯甲烷 、 乙酸乙酯 、 乙腈 为溶剂， -40.0~20.0 ℃ 、275.79 kPa 条件下， 反应 24.25h， 生成 2-O-benzyl-1,3-bis[(1,2-di-O-octanoyl-sn-glycero-3)-phosphoryl]glycerol di(2-cyanoethyl) ester
  参考文献：
  名称：

  Synthesis of short and long chain cardiolipins

  摘要：

  A phosphoramidite approach using 2-cyanoethyl N,N-diisopropylchlorophosphoramidite was utilized for the first time to synthesize short chain cardiolipins. The approach was extended to synthesize long chain and their ether analogue. Optically active 1,2-di-O-acylsn-glycerol or 1,2-di-O-myristyl-sn-glycerol was coupled with phosphoramidite reagent and 2-benzyloxy-1,3-propanediol in presence of 1H-tetrazole, followed by in situ oxidation, to give the corresponding protected cardiolipin analogues. The above intermediates were converted into cardiolipin analogues in two steps by deprotection of cyanoethyl and benzyl groups. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.04.071
• 作为产物：
  描述：

  辛酰氯 在 吡啶 、 4-二甲氨基吡啶 、 sodium hydride 作用下， 以 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 22.0h， 生成 (S)-sn-1,2-二辛酰-3-苄基甘油
  参考文献：
  名称：

  一种磷脂酸的制备工艺

  摘要：

  本发明属于有机合成技术领域，具体涉及一种磷脂酸的制备方法。本发明提供的磷脂酸的制备方法，包括以下步骤：(R)‑3‑氯‑1,2‑丙二醇与第一酰基化试剂进行第一酰基化反应，得到(R)‑3‑氯‑2‑羟基脂肪酸酯；再将其进行第二酰基化反应，得到(R)‑3‑氯‑1,2‑脂肪酸二酯；进而与苯甲醇发生取代反应后脱去苄基，最后进行磷酸酯化反应即可制备纯度≥98％的磷脂酸。本发明的工艺简洁，条件温和，适合工业化制备。

  公开号：

  CN115010749A

文献信息

• Synthesis and pharmacological evaluation of second-generation phosphatidic acid derivatives as lysophosphatidic acid receptor ligands
  作者：Gangadhar G. Durgam、Ryoko Tsukahara、Natalia Makarova、Michelle D. Walker、Yuko Fujiwara、Kathryn R. Pigg、Daniel L. Baker、Vineet M. Sardar、Abby L. Parrill、Gabor Tigyi、Duane D. Miller

  DOI：10.1016/j.bmcl.2005.10.031

  日期：2006.2

  pyrophosphate (DGPP 8:0, 1) and phosphatidic acid 8:0 (PA 8:0, 2), were previously identified as subtype-selective LPA(1) and LPA(3) receptor antagonists. Recently, we reported that the replacement of the phosphate headgroup by thiophosphate in a series of fatty alcohol phosphates (FAP) improves agonist as well as antagonist activities at LPA GPCR. Here, we report the synthesis of stereoisomers of PA 8:0 analogs

  短链磷脂酸衍生物，焦磷酸二辛酯甘油酯（DGPP 8：0，1）和磷脂酸8：0（PA 8：0，2）先前被确定为亚型选择性LPA（1）和LPA（3）受体拮抗剂。最近，我们报道了在一系列脂肪醇磷酸酯（FAP）中用硫代磷酸酯取代磷酸根基可以改善LPA GPCR的激动剂和拮抗剂活性。在这里，我们报告PA 8：0类似物的立体异构体的合成及其在LPA GPCR，PPARgamma和ATX的生物学评估。结果表明，LPA受体与甘油骨架修饰的配体立体选择性地相互作用。我们观察到由二辛基PA 8：0化合物产生的完全立体定向反应，其中（R）异构体是激动剂，（S）异构体是LPA GPCR的拮抗剂。从这个系列中 我们将化合物13b确定为最有效的LPA（3）受体亚型选择性激动剂（EC（50）= 3 nM），将8b确定为有效和选择性的LPA（3）受体拮抗剂（K（i）= 5 nM）和ATX抑制剂（IC（50）= 600 nM
• Cardiolipin molecules and methods of synthesis
  申请人：Ahmad U. Moghis

  公开号：US20050266068A1

  公开（公告）日：2005-12-01

  The invention provides new synthetic routes for cardiolipin with different fatty acids and/or alkyl chains with varying chain length and also with or without unsaturation, particularly a short-chain cardiolipin. The methods comprise reacting a 1,2-O-sn-diacyl/1,2-O-sn-dialkyl glycerol or a 2-O-protected glycerol, with a phosphoramidite reagent or a phosphate triester to produce a protected cardiolipin, which is deprotected to prepare the short chain cardiolipin. The reaction schemes can be used to generate new variants of cardiolipin. The cardiolipin prepared by the present methods can be incorporated into liposomes, which can also include active agents such as hydrophobic or hydrophilic drugs. Such liposomes can be used to treat diseases or in diagnostic and/or analytical assays. Liposomes can also include ligands for targeting a particular cell type or specific tissue.

  本发明提供了一种合成不同脂肪酸和/或不同链长烷基的心磷脂的新合成路线，以及具有或不具有不饱和度，特别是一种短链心磷脂。该方法包括将1,2-O-sn-二酰基/1,2-O-sn-二烷基甘油或2-O-保护甘油与磷酸酰胺试剂或磷酸三酯反应以产生受保护的心磷脂，然后去保护以制备短链心磷脂。该反应方案可用于生成心磷脂的新变体。通过本方法制备的心磷脂可以被纳入到脂质体中，这些脂质体还可以包括疏水性或亲水性药物等活性剂。这样的脂质体可以用于治疗疾病或在诊断和/或分析检测中使用。脂质体还可以包括用于靶向特定细胞类型或特定组织的配体。
• A synthesis of dioctanoyl phosphatidylinositol
  作者：Thomas S. Elliott、Joseph Nemeth、Simon A. Swain、Stuart J. Conway

  DOI：10.1016/j.tetasy.2009.11.026

  日期：2009.12

  A synthesis of the naturally occurring enantiomer of phosphatidylinositol is reported. A resolution strategy, using camphor as a chiral auxiliary is employed to obtain the desired, enantiomerically pure, inositol derivative. Dioctanoyl lipid chains are appended to the molecule, which are shorter than the naturally occurring lipid chains, providing the molecule with enhanced water solubility. (C) 2009 Elsevier Ltd. All rights reserved.
• Synthesis of L-α-Lecithins Containing Shorter Chain Fatty Acids. Water-soluble Glycerolphosphatides. I
  作者：Erich Baer、Vaidyanath Mahadevan

  DOI：10.1021/ja01519a051

  日期：1959.5
• Synthesis of short and long chain cardiolipins
  作者：Shoukath M. Ali、Moghis U. Ahmad、Peter Koslosky、Krishnudu Kasireddy、U. Murali Krishna、Imran Ahmad

  DOI：10.1016/j.tet.2006.04.071

  日期：2006.7

  A phosphoramidite approach using 2-cyanoethyl N,N-diisopropylchlorophosphoramidite was utilized for the first time to synthesize short chain cardiolipins. The approach was extended to synthesize long chain and their ether analogue. Optically active 1,2-di-O-acylsn-glycerol or 1,2-di-O-myristyl-sn-glycerol was coupled with phosphoramidite reagent and 2-benzyloxy-1,3-propanediol in presence of 1H-tetrazole, followed by in situ oxidation, to give the corresponding protected cardiolipin analogues. The above intermediates were converted into cardiolipin analogues in two steps by deprotection of cyanoethyl and benzyl groups. (c) 2006 Elsevier Ltd. All rights reserved.