Phenyl-tris(3-prop-2-ynoxypropyl)silane | 1415238-27-5

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: Phenyl-tris(3-prop-2-ynoxypropyl)silane
• 英文别名: phenyl-tris(3-prop-2-ynoxypropyl)silane
• CAS: 1415238-27-5
• 化学式: C₂₄H₃₂O₃Si
• 分子量: 396.602
• InChiKey: NYSSPIISNFQJAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.46
• 重原子数：
  28
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-[(2R,3R,4R,5S,6R)-2-(12-azidododecoxy)-6-(hydroxymethyl)-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl]acetamide 、 Phenyl-tris(3-prop-2-ynoxypropyl)silane 在 copper(II) sulfate 、 sodium ascorbate 作用下， 以 甲醇 、 水 为溶剂， 反应 24.0h， 以57.9%的产率得到N-[(2R,3R,4R,5S,6R)-2-[12-[4-[3-[bis[3-[[1-[12-[(2R,3R,4R,5S,6R)-3-acetamido-6-(hydroxymethyl)-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxydodecyl]triazol-4-yl]methoxy]propyl]-phenylsilyl]propoxymethyl]triazol-1-yl]dodecoxy]-6-(hydroxymethyl)-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl]acetamide
  参考文献：
  名称：

  Convenient assembly of trimeric Lex determinants using carbosilane scaffolds by means of Huisgen cycloaddition

  摘要：

  The Le(x) glycoside having an N-3 moiety at the omega position, which was prepared by using living cells from GlcNAcO(CH2)(12)N-3 as a starting material, was efficiently introduced into a trivalent-type carbosilane core scaffold by means of Huisgen cycloaddition reaction to yield the corresponding glycocluster having three Le(x) moieties at each end. Structural elucidation of the product was performed by a combination of NMR and mass spectroscopic analyses, and the results of the analyses supported the structure of the glycocluster. Evaluation of the glycocluster was carried out using Lotus lectin as a model lectin. Environmental changes of tryptophan residues located at or near the binding sites of Lotus lectin caused fluorescence intensity change. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.10.004
• 作为产物：
  描述：

  3-溴丙炔 、 3-[Bis(3-hydroxypropyl)-phenylsilyl]propan-1-ol 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以66.9%的产率得到Phenyl-tris(3-prop-2-ynoxypropyl)silane
  参考文献：
  名称：

  Convenient assembly of trimeric Lex determinants using carbosilane scaffolds by means of Huisgen cycloaddition

  摘要：

  The Le(x) glycoside having an N-3 moiety at the omega position, which was prepared by using living cells from GlcNAcO(CH2)(12)N-3 as a starting material, was efficiently introduced into a trivalent-type carbosilane core scaffold by means of Huisgen cycloaddition reaction to yield the corresponding glycocluster having three Le(x) moieties at each end. Structural elucidation of the product was performed by a combination of NMR and mass spectroscopic analyses, and the results of the analyses supported the structure of the glycocluster. Evaluation of the glycocluster was carried out using Lotus lectin as a model lectin. Environmental changes of tryptophan residues located at or near the binding sites of Lotus lectin caused fluorescence intensity change. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.10.004