(2S,3S,4R)-1-O-(6-deoxy-6-azido-α-D-galactopyranosyl)-2-[(N-nervonoyl)amino]octadecane-3,4-diol

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2S,3S,4R)-1-O-(6-deoxy-6-azido-α-D-galactopyranosyl)-2-[(N-nervonoyl)amino]octadecane-3,4-diol
• 英文别名: (Z)-N-[(2S,3S,4R)-1-[(2S,3R,4S,5R,6R)-6-(azidomethyl)-3,4,5-trihydroxyoxan-2-yl]oxy-3,4-dihydroxyoctadecan-2-yl]tetracos-15-enamide
• 化学式: C₄₈H₉₂N₄O₈
• 分子量: 853.28
• InChiKey: AWXATQZIMDXICW-WWHSRKRPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.1
• 重原子数：
  60
• 可旋转键数：
  42
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  163
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R)-1-O-(6-deoxy-6-azido-α-D-galactopyranosyl)-2-[(N-nervonoyl)amino]octadecane-3,4-diol 在 sodium acetate 、 三甲基膦 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 8.0h， 生成 (2S,3S,4R)-1-O-(6-deoxy-6-acetamido-α-D-galactopyranosyl)-2-(N-nervonoylamino)-1,3,4-octadecanetriol
  参考文献：
  名称：

  Synthesis of a Versatile Building Block for the Preparation of 6-N-Derivatized α-Galactosyl Ceramides: Rapid Access to Biologically Active Glycolipids

  摘要：

  A concise route to the 6-azido-6-deoxy-alpha-galactosyl-phytosphingosine derivative 9 is reported. Orthogonal protection of the two amino groups allows elaboration of 9 into a range of 6-N-derivatized alpha-galactosyl ceramides by late-stage introduction of the acyl chain of the ceramide and the 6-N-group in the sugar headgroup. Biologically active glycolipids 6 and 8 have been synthesized to illustrate the applicability of the approach.

  DOI：

  10.1021/jo102064p
• 作为产物：
  描述：

  糖脂 在 2,6-二甲基吡啶 、 偶氮二甲酸二异丙酯 、 叠氮磷酸二苯酯 、 sodium acetate 、 四丁基碘化铵 、 氟化氢吡啶 、 溶剂黄146 、 三乙胺 、 N,N-二异丙基乙胺 、 三苯基膦 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 20.83h， 生成 (2S,3S,4R)-1-O-(6-deoxy-6-azido-α-D-galactopyranosyl)-2-[(N-nervonoyl)amino]octadecane-3,4-diol
  参考文献：
  名称：

  Synthesis of a Versatile Building Block for the Preparation of 6-N-Derivatized α-Galactosyl Ceramides: Rapid Access to Biologically Active Glycolipids

  摘要：

  A concise route to the 6-azido-6-deoxy-alpha-galactosyl-phytosphingosine derivative 9 is reported. Orthogonal protection of the two amino groups allows elaboration of 9 into a range of 6-N-derivatized alpha-galactosyl ceramides by late-stage introduction of the acyl chain of the ceramide and the 6-N-group in the sugar headgroup. Biologically active glycolipids 6 and 8 have been synthesized to illustrate the applicability of the approach.

  DOI：

  10.1021/jo102064p

文献信息

• Synthesis of a Versatile Building Block for the Preparation of 6-<i>N</i>-Derivatized α-Galactosyl Ceramides: Rapid Access to Biologically Active Glycolipids
  作者：Peter J. Jervis、Liam R. Cox、Gurdyal S. Besra

  DOI：10.1021/jo102064p

  日期：2011.1.7

  A concise route to the 6-azido-6-deoxy-alpha-galactosyl-phytosphingosine derivative 9 is reported. Orthogonal protection of the two amino groups allows elaboration of 9 into a range of 6-N-derivatized alpha-galactosyl ceramides by late-stage introduction of the acyl chain of the ceramide and the 6-N-group in the sugar headgroup. Biologically active glycolipids 6 and 8 have been synthesized to illustrate the applicability of the approach.