N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-4-(n-dodecyloxymethyl)-1,2,3-triazolylacetamide | 1083009-30-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-4-(n-dodecyloxymethyl)-1,2,3-triazolylacetamide
• 英文别名: [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[[2-[4-(dodecoxymethyl)triazol-1-yl]acetyl]amino]oxan-2-yl]methyl acetate
• CAS: 1083009-30-6
• 化学式: C₃₁H₅₀N₄O₁₁
• 分子量: 654.758
• InChiKey: KKDDAQLBIQBMBO-OVFXHNNVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  46
• 可旋转键数：
  25
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  184
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-4-(n-dodecyloxymethyl)-1,2,3-triazolylacetamide 在 甲醇 、 sodium methylate 作用下， 以100%的产率得到N-β-D-glucopyranosyl-4-(n-dodecyloxymethyl)-1,2,3-triazolylacetamide
  参考文献：
  名称：

  Synthesis of novel glycolipids derived from glycopyranosyl azides and N-(β-glycopyranosyl)azidoacetamides

  摘要：

  A general and expedient method based on a click reaction has been developed for the synthesis of novel glycolipids. The Cu(I) catalyzed [3+2] cycloaddition of several fully acetylated beta- as well as alpha-D-glycopyranosyl azides, including the 1,6-diazide derived from D-glucose, with long chain alkyl propargyl ethers gave the respective 1,4-substituted 1,2,3-triazole derivatives in good yields. Treatment of fully acetylated N-(beta-glycopyranosyl)azidoacetamides under similar conditions with alkyl propargyl ethers afforded the 1,2,3-triazolylacetamido derivatives in fairly good yields. Zemplen de-O-acetylation of all the fully acetylated derivatives furnished the free glycolipids in quantitative yields. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.08.073
• 作为产物：
  描述：

  N-(2,3,4,6-tetra-O-acetylated-β-D-glucopyranosyl)azidoacetamide 、 n-dodecyl propargyl ether 在 copper diacetate 、 sodium ascorbate 作用下， 以 水 、 丙酮 为溶剂， 以70%的产率得到N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-4-(n-dodecyloxymethyl)-1,2,3-triazolylacetamide
  参考文献：
  名称：

  Synthesis of novel glycolipids derived from glycopyranosyl azides and N-(β-glycopyranosyl)azidoacetamides

  摘要：

  A general and expedient method based on a click reaction has been developed for the synthesis of novel glycolipids. The Cu(I) catalyzed [3+2] cycloaddition of several fully acetylated beta- as well as alpha-D-glycopyranosyl azides, including the 1,6-diazide derived from D-glucose, with long chain alkyl propargyl ethers gave the respective 1,4-substituted 1,2,3-triazole derivatives in good yields. Treatment of fully acetylated N-(beta-glycopyranosyl)azidoacetamides under similar conditions with alkyl propargyl ethers afforded the 1,2,3-triazolylacetamido derivatives in fairly good yields. Zemplen de-O-acetylation of all the fully acetylated derivatives furnished the free glycolipids in quantitative yields. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.08.073