(2S,3S)-2,3-epoxyoctadecan-1-ol | 136598-22-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: (2S,3S)-2,3-epoxyoctadecan-1-ol
• 英文别名: [(2S,3S)-3-pentadecyloxiran-2-yl]methanol
• CAS: 136598-22-6
• 化学式: C₁₈H₃₆O₂
• 分子量: 284.483
• InChiKey: YZFWQAZFXICNNE-ROUUACIJSA-N

物化性质

• 沸点：
  361.0±10.0 °C(Predicted)
• 密度：
  0.903±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  20
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  32.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S,3S)-2,3-epoxyoctadecan-1-ol 在 咪唑 、 sodium tetrahydroborate 、 二苯基二硒醚 、 双氧水 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 (2R,3E)-1-tert-butyldimethylsilyloxy-2-tert-butyldiphenylsilyloxy-3-octadecene
  参考文献：
  名称：

  Mori, Kenji; Uenishi, Keiji, Liebigs Annalen der Chemie, 1994, # 1, p. 41 - 48

  摘要：

  DOI：
• 作为产物：
  描述：

  (E)-2-十八烯醇 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 (+)-Weinsaeure-diethylester 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 48.0h， 以19.2 g的产率得到(2S,3S)-2,3-epoxyoctadecan-1-ol
  参考文献：
  名称：

  Mori, Kenji; Uenishi, Keiji, Liebigs Annalen der Chemie, 1994, # 1, p. 41 - 48

  摘要：

  DOI：

文献信息

• Syntheses and characterization of four diastereomers of trehalose-6, 6′-dicorynomycolates (TD BH32)
  作者：Mugio Nishizawa、Ryutaro Minagawa、Dulce M. Garcia、Susumi Hatakeyama、Hidetoshi Yamada

  DOI：10.1016/s0040-4039(00)78212-8

  日期：1994.8

  Four diastereomers of trehalose-6,6'-dicorynomycolates (TD BH-32) have been synthesized selectively by DCC/DMAP.HCl mediated diesterification of protected trehalose with corynomicolic acid and its all possible isomers, each of which was prepared in enantiomerically pure form.
• Molecular Interactions and Functional Interference between Vitronectin and Transforming Growth Factor-β
  作者：Michael Schoppet、Triantafyllos Chavakis、Nadia Al-Fakhri、Sandip M Kanse、Klaus T Preissner

  DOI：10.1038/labinvest.3780393

  日期：2002.1

  Different extracellular matrix proteins have been described as binding proteins for growth factors, influencing their storage or presentation towards cellular receptors. The multifunctional adhesive glycoprotein vitronectin (VN), which is found in the circulation and widely distributed throughout different tissues, has been implicated in the regulation of vascular cell functions, and these activities could be related to interactions with various growth factors. In vitro, soluble VN interfered with transforming growth factor-beta (TGF-beta) binding to isolated extracellular matrix and was found to associate with TGF-beta1 and TGF-beta2 as well as with other growth factors such as vascular endothelial growth factor, epidermal growth factor, or basic fibroblast growth factor in a saturable manner. In particular, binding of TGF-beta was maximal for the heparin-binding multimeric isoform of VN, whereas VN in a ternary complex with thrombin and antithrombin or plasma VN exhibited weaker binding. Plasminogen activator inhibitor-1 (PAI-1) or heparin, but not desulfated glycosaminoglycans, interfered with binding of VN to TGF-beta, and soluble PAI-1 was able to dissociate VN-bound TGF-beta. Upon limited plasmin proteolysis of VN, only the fragments comprising the intact aminoterminal portion of VN bound to TGF-beta as did a synthetic peptide (amino acids 43 to 62), indicating that TGF-beta and PAI-1 share common binding site(s) on VN. Although VN did not influence TGF-beta bioactivity for mink lung epithelial cells, TGF-beta dose dependently inhibited both urokinase-receptor as well as alpha(v)-integrin-dependent adhesion to VN. This activity of TGF-beta was reminiscent of the antiadhesive function of PAI-1. In atherosclerotic tissue sections, staining patterns of VN and TGF-beta indicated their colocalization. These findings describe VN as a new binding protein for TGF-beta, whereby specific functions of both factors become modulated by this interaction.
• Mori, Kenji; Uenishi, Keiji, Liebigs Annalen der Chemie, 1994, # 1, p. 41 - 48
  作者：Mori, Kenji、Uenishi, Keiji

  DOI：——

  日期：——