1-mesyloxy-5-tetrahydropyranyloxy-pentane | 76102-75-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 1-mesyloxy-5-tetrahydropyranyloxy-pentane
• 英文别名: 1-(methanesulfonoxy)-5-<(tetrahydropyran-2-yl)oxy>pentane；5-<(tetrahydro-2H-pyran-2-yl)oxy>pentyl methanesulfonate；5-(tetrahydropyran-2-yloxy)pentane-1-methanesulfonate；5-tetrahydropyranyloxypentanol methanesulfonate；1-<5-<2-(tetrahydropyranyloxy)>pentyl>methanesulfonate；5-(Oxan-2-yloxy)pentyl methanesulfonate
• CAS: 76102-75-5
• 化学式: C₁₁H₂₂O₅S
• 分子量: 266.359
• InChiKey: YEBDFNKTBGHKCW-UHFFFAOYSA-N

物化性质

• 沸点：
  417.6±40.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  70.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-mesyloxy-5-tetrahydropyranyloxy-pentane 在 4-甲基苯磺酸吡啶 、 sodium hydride 作用下， 以 甲醇 为溶剂， 反应 9.0h， 生成 5-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-Heptadecafluoro-1-nonyl-undecyloxy)-pentan-1-ol
  参考文献：
  名称：

  New anionic glycophospholipids with two perfluorocarbon or two hydrocarbon or mixed hydrophobic chains

  摘要：

  Novel amphiphilic anionic sugar phosphates esterified by various hydrophobic double-chain tails were synthesized. They differ primarily by the design of their hydrophobic tail. Amphiphile 12a derives from phosphogalactose and has two perfluoroalkylated hydrophobic chains; 12b has a pentenyloxy spacer between the mixed hydrocarbon/fludrocarbon double-chain and the same head group; 12c and 14c are galactose and glucose derivatives with two hydrocarbon tail chains. All were prepared through a three-step H-phosphonate route: reaction of the hydrophobic double-chain alcohol on phosphorus trichloride (27-60%), followed by the addition of the appropriately protected sugar, by oxidation (50-81%), and finally by deprotection of the sugar (58-95%). The starting alcohols were prepared through conventional reactions. Their synthesis was however, difficult, essentially as a result of lesser reactivity, and of low solubility of some of the intermediates related to the presence of the bulky, strongly hydrophobic chains. Preliminary biocompatibility assays indicate a reduction in hemolytic activity by increasing the number of fluorinated chains or by increasing the total length, hence the hydrophobicity of the amphiphile. Acute toxicity tests indicate maximum intravenously tolerated doses in mice of ca. 500 mg/kg body weight for 12a and 12b.

  DOI：

  10.1016/0009-3084(95)02492-2
• 作为产物：
  描述：

  1,5-戊二醇 在 盐酸 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 50.0h， 生成 1-mesyloxy-5-tetrahydropyranyloxy-pentane
  参考文献：
  名称：

  通过三脚架-三脚架偶合直接大环合成来合成大环多胺

  摘要：

  五个macrobicyclic多胺合成1 - 5，其中macrobicycle由两个三足亚基的结合而形成的路线以下进行说明。这样的序列明显比通过大环的逐步构建短，并且可以提供更高的产率，如通过二种途径合成的双-tren 3的情况所示。

  DOI：

  10.1002/hlca.19850680202

文献信息

• Improved Th17 Selectivity of α-Galactosylceramide via Noncovalent Interactions with Diether Moiety
  作者：Yoon Soo Hwang、Junhyeong Yim、Heebum Song、Seung Bum Park

  DOI：10.1021/acsmedchemlett.8b00556

  日期：2019.5.9

  α-Galactosylceramide (α-GalCer) is a typical antigen for invariant natural killer T cells that are a subset of T cells and play critical roles in regulating immune responses. To selectively induce the secretion of certain cytokines via introducing hydrogen-bonding interaction with polar amino acid residues in the binding pocket of CD1d, a series of α-GalCer analogues with diether moiety in the acyl chain

  α-半乳糖苷神经酰胺（α-GalCer）是不变的自然杀伤性T细胞的一种典型抗原，后者是T细胞的子集，在调节免疫应答中起关键作用。为了通过在CD1d的结合口袋中引入与极性氨基酸残基的氢键相互作用，选择性地诱导某些细胞因子的分泌，设计并合成了一系列在酰基链中带有二醚部分的α-GalCer类似物。这些类似物的后续体外生物学评估揭示了选择性IL-17分泌的结构-活性关系。类似物5和6比其他细胞因子诱导IL-17分泌显着增加，表明对病原体具有保护作用。相反，类似物7显示出高度减少的IL-17分泌，这可能表明潜在的抗炎作用。
• Synthesis of structural analogues of leukotriene B4 and their receptor binding activity
  作者：Mitoshi Konno、Takahiko Nakae、Shigeru Sakuyama、Minoru Nishizaki、Yoshihiko Odagaki、Hisao Nakai、Nobuyuki Hamanaka

  DOI：10.1016/s0968-0896(97)00090-4

  日期：1997.8

  [3H] LTB4 binding to human neutrophils, and by a secondary intact human neutrophil functional assay for agonist/antagonist activity. The first analogues prepared, compounds 2-7, demonstrated moderate potency in the LTB4 receptor binding assay. The modification of these compounds by the introduction of another substituent into the aromatic ring produced a marked increase in receptor binding (28c, IC50

  白三烯B4（LTB4）的结构类似物是根据LTB4的合理构象设计的（1）。将构象体A或B的C-7-C-9连接到芳香环系统中，导致发现苯类似物2、4和6a。将构象体C或D的C-4-C-9连接到芳香环系统中，导致发现类似物3、5和7。评估了本研究中化合物对[3H] LTB4结合的抑制作用人类嗜中性粒细胞，并通过第二次完整的人类嗜中性粒细胞功能测定来确定激动剂/拮抗剂活性。制备的第一个类似物化合物2-7在LTB4受体结合试验中显示出中等效力。通过将另一个取代基引入芳环对这些化合物进行修饰，可显着提高受体结合力（28c，IC50 = 0.020 microM; 38c，IC50 = 0。020微米; 52a，IC 50 ＝0.020μM；52b，IC 50 ＝0.018μM。LTB4的大多数这些结构类似物表现出激动剂活性。在这项研究中制备的类似物中，只有化合物57在10 microM时显示出弱的LTB4受体拮抗剂活性。
• Synthesis and structural studies of bridgehead dienes
  作者：K.J. Shea、L.D. Burke、Robert J. Doedens

  DOI：10.1016/s0040-4020(01)87603-1

  日期：1986.1

  Single crystal X-ray structures of two bridgehead dienes are reported. The bridgehead double bonds of diene 7 show only modest deviation from strain-free tetrasubstituted double bonds. The double bonds in bridgehead diene 6, however, exhibit an average deviation of the C—CC—C torsion angle (φ + χ) of 14°.

  报道了两个桥头二烯的单晶X射线结构。二烯7的桥头双键仅显示出与无应变的四取代双键的适度偏差。然而，桥头二烯6中的双键表现出CC-C-CC扭转角（φ+χ）的平均偏差为14°。
• Vig, O. P.; Sharma, M. L.; Verma, N. K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1981, vol. 20, # 10, p. 860 - 862
  作者：Vig, O. P.、Sharma, M. L.、Verma, N. K.、Malik, Neera

  DOI：——

  日期：——
• Intramolecular cycloaddition reactions of dienyne ethers. Synthesis of bridgehead dienes and their thermal rearrangements
  作者：K. J. Shea、L. D. Burke

  DOI：10.1021/jo00237a019

  日期：1988.1