di-O,O'-hexadecylpentaerythritol | 127424-61-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: di-O,O'-hexadecylpentaerythritol
• 英文别名: di-O-hexadecyl pentaerythritol；2,2-dihexadecyloxymethyl-1,3-propanediol；2,2-Bis(hexadecoxymethyl)propane-1,3-diol
• CAS: 127424-61-7
• 化学式: C₃₇H₇₆O₄
• 分子量: 585.008
• InChiKey: MFZQZRCJNUTPQY-UHFFFAOYSA-N

物化性质

• 熔点：
  69-70 °C
• 沸点：
  657.8±55.0 °C(Predicted)
• 密度：
  0.904±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  14.2
• 重原子数：
  41
• 可旋转键数：
  36
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  di-O,O'-hexadecylpentaerythritol 在 吡啶 、 4-二甲氨基吡啶 、 2,6-二叔丁基-4-甲基吡啶 、 1-(苯基亚硫酰基)哌啶 、 camphor-10-sulfonic acid 、 二正丁基氧化锡 、 trifluoromethanesulfonic acid anhydride 、 2,2-二甲基-1,3-丙二醇 作用下， 以 二氯甲烷 、 苯 为溶剂， 生成 3-benzyloxy-2,2-dihexadecyloxymethylpropyl 6-O-benzoyl-2,3-di-O-benzyl-β-D-mannopyranoside
  参考文献：
  名称：

  β-1,4-二-d-甘露糖醛酸糖苷的合成作为toll样受体的潜在配体

  摘要：

  Toll样受体（TLR）在宿主免疫防御中起着重要作用，合成的TLR配体是治疗多种疾病（包括感染，炎症和癌症）的有用治疗剂。藻酸盐是由TLR2 / 4介导的强免疫刺激剂。这里报道的是两个衍生自海藻酸盐的β-1,4-二-d-甘露糖醛酸部分的糖苷（1和2）的设计和化学合成。该合成的特征在于，通过对映体选择性地对4,6-二-O-亚苄基保护的硫代甘露糖苷供体7进行非对映选择性β-糖基化，然后使用TEMPO / BAIB进行氧化，以提供β- 1,4-二-d-甘露糖醛酸部分。

  DOI：

  10.1016/j.tetlet.2007.02.086
• 作为产物：
  描述：

  3,3-dihexadecyloxymethyl-1,5-dioxaspiro[5.5]undecan 在 camphor-10-sulfonic acid 、 2,2-二甲基-1,3-丙二醇 作用下， 以 二氯甲烷 为溶剂， 以95%的产率得到di-O,O'-hexadecylpentaerythritol
  参考文献：
  名称：

  β-1,4-二-d-甘露糖醛酸糖苷的合成作为toll样受体的潜在配体

  摘要：

  Toll样受体（TLR）在宿主免疫防御中起着重要作用，合成的TLR配体是治疗多种疾病（包括感染，炎症和癌症）的有用治疗剂。藻酸盐是由TLR2 / 4介导的强免疫刺激剂。这里报道的是两个衍生自海藻酸盐的β-1,4-二-d-甘露糖醛酸部分的糖苷（1和2）的设计和化学合成。该合成的特征在于，通过对映体选择性地对4,6-二-O-亚苄基保护的硫代甘露糖苷供体7进行非对映选择性β-糖基化，然后使用TEMPO / BAIB进行氧化，以提供β- 1,4-二-d-甘露糖醛酸部分。

  DOI：

  10.1016/j.tetlet.2007.02.086

文献信息

• Synthesis and Liquid Crystalline Properties of Mono-, Di- and Tri-O-alkyl Pentaerythritol Derivatives Bearing Tri-, Di- or Monogalactosyl Heads: The Effects of Curvature of Molecular Packing on Mesophase Formation
  作者：Fabienne Dumoulin、Dominique Lafont、Thai-Lê Huynh、Paul Boullanger、Grahame Mackenzie、Jon J. West、John W. Goodby

  DOI：10.1002/chem.200601702

  日期：2007.6.25

  dependency of lyotropic liquid crystals with those of thermotropic liquid crystals. In order to undertake this systematic study a range of different pentaerythritol derivatives was synthesized, which covers combinations of one to three alkyl chains of different lengths (6,7,9,10,11,12,14,16 carbon atoms) and three to one galactosyl heads. Mono- and di-O-galactosyl derivatives were prepared directly

  自组织和自组装对于合成膜和生物膜的稳定性至关重要。特别重要的是考虑各种分子种类的填充排列。磷脂和糖脂都可以通过将曲率引入自组织或自组装系统的方式堆积。例如，已知弯曲度会影响所形成的任何凝结相的结构。在本文中，我们报告了一项系统研究，其中我们改变了糖脂的形状并检查了糖脂形成的缩合相。在此过程中，我们还将溶致液晶的形状依赖性和热致液晶的形状依赖性结合在一起。为了进行这项系统的研究，合成了一系列不同的季戊四醇衍生物，它涵盖了1至3个不同长度（6、7、9、10、11、12、14、16个碳原子）的烷基链和3至1个半乳糖基头的组合。单-和二-O-半乳糖基衍生物是通过使用2,3,4,6-四-O-苯甲酰基或乙酰基-α-D-吡喃半乳糖基三氯乙酰亚氨酸酯或溴化物作为供体，通过相应醇的糖基化直接制备的；由O-烷基-O-苄基二O-半乳糖基季戊四醇中间体合成三-O-半乳糖基衍生物，然后进行去-O-苄基化和糖基化步骤
• Synthesis of Glycolipid Clusters with Pentaerythritol Cores and Different Ethyleneoxy-Spaced Mannose Residues as Terminal Carbohydrates
  作者：Matthias Schmidt、Bodo Dobner、Peter Nuhn

  DOI：10.1002/1099-0690(200202)2002:4<669::aid-ejoc669>3.0.co;2-n

  日期：2002.2

  We describe the synthesis of polyantennary glycolipid clusters with pentaerythritol cores. A known protecting group strategy permits the introduction of different hydrophobic moieties and the selective coupling with ethyleneoxy spacers of different lengths. After glycosidation, substances with one, two or three mannose residues as terminal carbohydrate headgroups were isolated. These polyantennary

  我们描述了具有季戊四醇核心的多触角糖脂簇的合成。已知的保护基策略允许引入不同的疏水部分和与不同长度的亚乙基氧基间隔物的选择性偶联。糖苷化后，分离出具有 1、2 或 3 个甘露糖残基作为末端碳水化合物头基的物质。这些多触角甘露糖苷可用作将脂质体靶向巨噬细胞甘露糖受体的有吸引力的工具。
• Synthesis and interfacial behaviour of a gemini neoglycolipid
  作者：S Chierici、P Boullanger、L Marron-Brignone、R.M Morelis、P.R Coulet

  DOI：10.1016/s0009-3084(97)00029-7

  日期：1997.7

  A gemini neoglycolipid was synthetised from pentaerythritol as the central building block to which were coupled two lipid moieties (C16H33 alkyl chains). The subsequent glycosylation reaction with two carbohydrate units (beta-D-GlcNAc) was achieved in acceptable yields which were, nevertheless, much lower than those obtained with the single-chain homologous derivatives. The behaviour of this neoglycolipid in monolayer was studied in details after spreading at an air/water interface. These molecules exhibit transition phases when the monolayer is compressed, revealing a similar behaviour to that of phospholipids. The behaviour of neoglycolipid 1 suggests a peculiar conformation at the air/water interface. This supramolecular arrangement might be taken as a model for molecular recognition of glycolipids in organized systems. (C) 1997 Elsevier Science Ireland Ltd.
• Synthesis of β-(1→4)-oligo-d-mannuronic acid neoglycolipids
  作者：Rongsong Xu、Zi-Hua Jiang

  DOI：10.1016/j.carres.2007.10.007

  日期：2008.1

  Mammalian Toll-like receptors (TLRs) play important roles in host immune defense. The activation of TLR and downstream signaling pathways have great impact on human physiology. Chemically diverse microbial products as well as synthetic ligands serve as agonists for these receptors. Recently, synthetic TLR ligands are being exploited as useful therapeutic agents for a variety of diseases including infections, inflammatory diseases, and cancers. Alginate polymers and oligosaccharides are strong immune stimulants mediated by TLR2/4, but synthesis of alginate oligomers is rarely studied. Reported here are the design and chemical synthesis of two beta-(1 -> 4)-di- and beta-(1 -> 4)-tri-D-mannuronic acid neoglycolipids 1 and 2 as potential TLR ligands. By using 4,6-di-O-benzylidene-protected 1-thio mannoside 7 as a glycosyl donor, the diastereoselective beta-D-mannosylation protocol provides the beta-(1 -> 4)-D-mannobiose and beta-(1 -> 4)-D-mannotriose derivatives, which upon regioselective oxidation with TEMPO/BAIB oxidation system yield the corresponding beta-(1 -> 4)-D-mannuronic acid containing neoglycolipids 1 and 2. (c) 2007 Elsevier Ltd. All rights reserved.