4-[3-(perfluorooctyl)propyloxy]-cis-2-butenyl alcohol | 908833-68-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-[3-(perfluorooctyl)propyloxy]-cis-2-butenyl alcohol
• 英文别名: (Z)-4-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecoxy)but-2-en-1-ol
• CAS: 908833-68-1
• 化学式: C₁₅H₁₃F₁₇O₂
• 分子量: 548.24
• InChiKey: LRXJDUAPACDYNZ-UPHRSURJSA-N

物化性质

• 沸点：
  306.3±42.0 °C(Predicted)
• 密度：
  1.495±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  34
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  4-[3-(perfluorooctyl)propyloxy]-cis-2-butenyl alcohol 在 甲醇 、 丙烷-1-硫醇 、 triphenylbismuth ditriflate 、 sodium 作用下， 以 二氯甲烷 为溶剂， 反应 4.67h， 生成
  参考文献：
  名称：

  五价铋作为通用促进剂，用于含硫醇添加剂的含S糖基供体

  摘要：

  发现在三小时内在丙硫醇作为添加剂存在下，活化程度较低的糖（例如过乙酰化的碳水化合物和糖醛酸酯类）的S-丙基糖苷以前无法单独用三苯基铋三氟甲磺酸酯活化，因此被糖基化。还发现该新开发的方案可有效促进S-苯基，S-噻唑啉基，S-苯并恶唑基和S-金刚烷基糖苷以及唾液酸的中性和糖醛酸酯的糖基化。

  DOI：

  10.1021/acs.orglett.7b02080
• 作为产物：
  描述：

  3-全氟辛基丙醇 在 四丁基溴化铵 、 三乙胺 、 potassium hydroxide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 4-[3-(perfluorooctyl)propyloxy]-cis-2-butenyl alcohol
  参考文献：
  名称：

  Fluorous-based carbohydrate Quartz Crystal Microbalance

  摘要：

  Fluorous chemistry has brought many applications from catalysis to separation science, from supramolecular materials to analytical chemistry. However, fluorous-based Quartz Crystal Microbalance (QCM) has not been reported so far. In the current paper, fluorous interaction has been firstly utilized in QCM, and carbohydrate-protein interaction and carbohydrate-carbohydrate interaction have been detected afterward. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2014.07.023

文献信息

• Noncovalent fluorous interactions for the synthesis of carbohydrate microarrays
  作者：Sreeman K. Mamidyala、Kwang-Seuk Ko、Firoz A. Jaipuri、Gisun Park、Nicola L. Pohl

  DOI：10.1016/j.jfluchem.2006.01.001

  日期：2006.5

  A surface patterning method based on noncovalent immobilization of fluorous-tagged sugars on fluorous-derivatized glass slides allows the facile fabrication of carbohydrate microarrays. To expand the scope of these arrays, the first syntheses are reported of arabinose, rhamnose, lactose, maltose, and glucosamine tagged with a single C8F17-tail for ease of purification as well as array formation. Screening

  一种基于氟标签化的糖在氟衍生化的载玻片上的非共价固定化的表面图案化方法，可轻松制造碳水化合物微阵列。为了扩大这些阵列的范围，报道了用单个C 8 F 17尾标记的阿拉伯糖，鼠李糖，乳糖，麦芽糖和葡糖胺的首次合成，以易于纯化和形成阵列。对来自普通小麦（WGA）和花生花生（PNA）的凝集素的这些碳水化合物微阵列的筛选表明，在生物学测定条件下，非共价氟-氟相互作用足以保留单糖和二糖。
• Mono- vs. di-fluorous-tagged glucosamines for iterative oligosaccharide synthesis
  作者：Gisun Park、Kwang-Seuk Ko、Aleksandra Zakharova、Nicola L. Pohl

  DOI：10.1016/j.jfluchem.2008.05.001

  日期：2008.10

  cartridge using simple gravity filtration to separate the desired product from the singly-fluorous-tagged starting materials and their decomposition products. In addition, removal of the fluorous acetate and its byproducts after sodium methoxide treatment and neutralization required only dissolution of the desired sugar in toluene and subsequent removal of the toluene layer from the denser fluorous byproducts

  含氟标签的保护基团是在寡糖合成中延长碳水化合物链的有吸引力的工具。为了消除在自动寡糖合成条件下失败序列的积累，额外的 C(8)F(17) 酯衍生保护基团连接到糖基供体，以更好地保留所需的双标签糖基化产物在氟固相萃取 (FSPE) 上) 墨盒。初步研究表明，双氟标记策略提供了足够强大的分离，使用商业 FSPE 小柱使用简单的重力过滤将所需产物与单氟标记起始材料及其分解产物分离。此外，
• Protecting-Group-Based Colorimetric Monitoring of Fluorous-Phase and Solid-Phase Synthesis of Oligoglucosamines
  作者：Kwang-Seuk Ko、Gisun Park、Yang Yu、Nicola L. Pohl

  DOI：10.1021/ol802229b

  日期：2008.12.4

  A new hydroxyl protecting group, nitrophthalimidobutyric (NPB) acid, has been synthesized in one solvent-free step for colorimetric monitoring of reaction cycles upon its facile removal with hydrazine acetate in the solid-phase and fluorous-phase syntheses of antigenic oligoglucosamines associated with infectious Staphylococcus aureus. The NPB group serves as a convenient hydroxyl protecting group that is stable to the basic conditions required for the synthesis of the common trichloroacetimidate protecting groups, the strongly acidic conditions used in glycosylation reactions, as well as conditions commonly used to remove silicon-based protecting groups.
• Automated Solution-Phase Synthesis of β-1,4-Mannuronate and β-1,4-Mannan
  作者：Shu-Lun Tang、Nicola L. B. Pohl

  DOI：10.1021/acs.orglett.5b01013

  日期：2015.6.5

  The first automated solution-phase synthesis of beta-1,4-mannuronate and beta-1,4-mannan oligomers has been accomplished by using a beta-directing C-5 carboxylate strategy. By utilizing fluorous-tag assisting purification after repeated reaction cycles, beta-1,4-mannuronate was synthesized up to a hexasaccharide with limited loading of a glycosyl donor (up to 3.5 equiv) for each glycosylation cycle due to the homogeneous solution-phase reaction condition. After a global reduction of the uronates, the beta-1,4-mannan hexasaccharide was obtained, thereby demonstrating a new approach to beta-mannan synthesis.
• Automated Solution-Phase Synthesis of Insect Glycans to Probe the Binding Affinity of Pea Enation Mosaic Virus
  作者：Shu-Lun Tang、Lucas B. Linz、Bryony C. Bonning、Nicola L. B. Pohl

  DOI：10.1021/acs.joc.5b01428

  日期：2015.11.6

  Pea enation mosaic virus (PEMV)-a plant RNA virus transmitted exclusively by aphids-causes disease in multiple food crops. However, the aphid-virus interactions required for disease transmission are poorly understood. For virus transmission, PEMV binds to a heavily glycosylated receptor aminopeptidase N in the pea aphid gut and is transcytosed across the gut epithelium into the aphid body cavity prior to release in saliva as the aphid feeds. To investigate the role of glycans in PEMV-aphid interactions and explore the possibility of viral control through blocking a glycan interaction, we synthesized insect N-glycan terminal trimannosides by automated solution-phase synthesis. The route features a mannose building block with C-5 ester enforcing a beta-linkage, which also provides a site for subsequent chain extension. The resulting insect N-glycan terminal trimannosides with fluorous tags were used in a fluorous microarray to analyze binding with fluorescein isothiocyanate-labeled PEMV; however, no specific binding between the insect glycan and PEMV was detected. To confirm these microarray results, we removed the fluorous tag from the trimannosides for isothermal titration calorimetry studies with unlabeled PEMV. The ITC studies confirmed the microarray results and suggested that this particular glycan-PEMV interaction is not involved in virus uptake and transport through the aphid.