(2S,3S,4R)-2-[(N-tert-butoxycarbonyl)amino]-3,4-di-tert-butyldimethylsilyloxy-1-O-(6-deoxy-6-azido-2,3,4-tri-O-trimethylsilyl-α-D-galactopyranosyl)octadecane | 1260236-39-2

• 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)-2-[(N-tert-butoxycarbonyl)amino]-3,4-di-tert-butyldimethylsilyloxy-1-O-(6-deoxy-6-azido-2,3,4-tri-O-trimethylsilyl-α-D-galactopyranosyl)octadecane
• 英文别名: tert-butyl N-[(2S,3S,4R)-1-[(2S,3R,4S,5S,6R)-6-(azidomethyl)-3,4,5-tris(trimethylsilyloxy)oxan-2-yl]oxy-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]octadecan-2-yl]carbamate
• CAS: 1260236-39-2
• 化学式: C₅₀H₁₀₈N₄O₉Si₅
• 分子量: 1049.86
• InChiKey: YEYFNEACAFUMHH-INOBHUGISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.46
• 重原子数：
  68
• 可旋转键数：
  35
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.98
• 拓扑面积：
  117
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R)-2-[(N-tert-butoxycarbonyl)amino]-3,4-di-tert-butyldimethylsilyloxy-1-O-(6-deoxy-6-azido-2,3,4-tri-O-trimethylsilyl-α-D-galactopyranosyl)octadecane 在 sodium acetate 、 三氟乙酸 、 三甲基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.24h， 生成 1-O-(6-benzureido-6-deoxy-α-D-galactopyranosyl)-2-hexacosylamino-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 、 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 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 18.25h， 生成 (2S,3S,4R)-2-[(N-tert-butoxycarbonyl)amino]-3,4-di-tert-butyldimethylsilyloxy-1-O-(6-deoxy-6-azido-2,3,4-tri-O-trimethylsilyl-α-D-galactopyranosyl)octadecane
  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.