trimethylsilyl 6-deoxy-6-azido-2,3,4-tri-O-trimethylsilyl-α-D-galactopyranoside | 1260236-42-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: trimethylsilyl 6-deoxy-6-azido-2,3,4-tri-O-trimethylsilyl-α-D-galactopyranoside
• 英文别名: [(2R,3S,4S,5R,6R)-2-(azidomethyl)-3,5,6-tris(trimethylsilyloxy)oxan-4-yl]oxy-trimethylsilane
• CAS: 1260236-42-7
• 化学式: C₁₈H₄₃N₃O₅Si₄
• 分子量: 493.899
• InChiKey: JHCASWABWJASCR-DISONHOPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.53
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  60.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1,2,3,4-tetra-O-trimethylsilyl-α-D-galactopyranose 在 偶氮二甲酸二异丙酯 、 叠氮磷酸二苯酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 以87%的产率得到trimethylsilyl 6-deoxy-6-azido-2,3,4-tri-O-trimethylsilyl-α-D-galactopyranoside
  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.