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 | 1415238-28-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 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
• CAS: 1415238-28-6
• 化学式: C₃₂H₅₈N₄O₁₅
• 分子量: 738.83
• InChiKey: SQVOOZMRIBCZQQ-HDEGJJDMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  51
• 可旋转键数：
  21
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  261
• 氢给体数：
  9
• 氢受体数：
  17

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：

  12-azidododecyl 2-acetamido-2-deoxy-β-D-glucopyranoside 在 Human promyelocytic leukemia cells 作用下， 生成 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
  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

文献信息

• Convenient assembly of trimeric Lex determinants using carbosilane scaffolds by means of Huisgen cycloaddition
  作者：Koji Matsuoka、Hiroki Yamaguchi、Tatsuya Kohzu、Jun-Ichi Sakamoto、Tetsuo Koyama、Ken Hatano、Shigeto Yamamoto、Tsutomu Mori、Kenichi Hatanaka

  DOI：10.1016/j.tetlet.2012.10.004

  日期：2012.12

  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.